CN112430232B - Heterocyclic compound and organic light-emitting element comprising same - Google Patents

Heterocyclic compound and organic light-emitting element comprising same Download PDF

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CN112430232B
CN112430232B CN202011103242.5A CN202011103242A CN112430232B CN 112430232 B CN112430232 B CN 112430232B CN 202011103242 A CN202011103242 A CN 202011103242A CN 112430232 B CN112430232 B CN 112430232B
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CN112430232A (en
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车龙范
李东勋
赵圣美
郑珉祐
李征夏
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LG Chem Ltd
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Abstract

The present invention relates to a heterocyclic compound and an organic light-emitting element including the same. The heterocyclic compound of the present invention can be used as a material for an organic layer of an organic light-emitting element, and by using the heterocyclic compound, an improvement in efficiency, a low driving voltage, and/or life characteristics of the organic light-emitting element can be achieved.

Description

Heterocyclic compound and organic light-emitting element comprising same
The present application is a divisional application of chinese patent application with the application number of "201710383655.5" and the name of "heterocyclic compound and organic light-emitting element containing the same", which is the application day of 2017, 5 and 26.
Technical Field
The present application claims priority from korean patent application No. 10-2016-0066652, filed in the korean patent office at 5/30 of 2016, the contents of which are all hereby incorporated by reference.
The present specification relates to a heterocyclic compound and an organic light-emitting element including the same.
Background
In general, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by 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 and an organic layer therebetween. In order to improve efficiency and stability of the organic light-emitting element, the organic layer may be formed of a multilayer structure of different materials, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light-emitting element, 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, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition again to the ground state.
There is a continuing need to develop new materials for use in organic light emitting elements as described above.
Prior art literature
Patent literature
U.S. patent application publication No. 2004-0251816
Disclosure of Invention
The present specification provides heterocyclic compounds and organic light-emitting elements comprising 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 above-mentioned chemical formula 1,
l1 and L2 are identical or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
x1 is N or CR3, X2 is N or CR4, X3 is N or CR5,
at least one of X1 to X3 is N,
r1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, nitrile, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkyl sulfoxide, substituted or unsubstituted aryl sulfoxide, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amino, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
Ar1 is a group represented by any one of the following formulas a to h,
[ chemical formula a ]
In the above-mentioned chemical formula a,
y1 is a direct bond, or-C (R6R 7) -,
q1 to Q8 are the same or different from each other and are each independently hydrogen, deuterium, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amide group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkyl sulfoxide group, substituted or unsubstituted aryl sulfoxide group, substituted or unsubstituted alkenyl group, substituted or unsubstituted silyl group, substituted or unsubstituted boron group, substituted or unsubstituted amine group, substituted or unsubstituted arylphosphine group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group, or groups adjacent to each other may be combined with each other to form a substituted or unsubstituted ring,
[ chemical formula b ]
In the above-mentioned chemical formula b,
u1 is a substituted or unsubstituted aryl group,
q9 and Q10 are hydrogen or may combine with each other to form a substituted or unsubstituted ring,
q9 is an integer of 1 to 3,
q10 is an integer of 1 to 4,
when q9 and q10 are each plural, the structures in plural brackets are the same or different from each other,
[ chemical formula c ]
In the above-mentioned chemical formula c,
u2 is a substituted or unsubstituted aryl group,
q11 to Q13 are the same or different from each other and are each independently hydrogen, deuterium, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amide group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkyl sulfoxide group, substituted or unsubstituted aryl sulfoxide group, substituted or unsubstituted alkenyl group, substituted or unsubstituted silyl group, substituted or unsubstituted boron group, substituted or unsubstituted amine group, substituted or unsubstituted arylphosphine group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group, or groups adjacent to each other may be combined with each other to form a substituted or unsubstituted ring,
q11 is either 1 or 2 and,
q13 is an integer of 1 to 4,
when q11 and q13 are each plural, the structures in plural brackets are the same or different from each other,
[ chemical formula d ]
[ chemical formula e ]
In the above-mentioned chemical formulas d and e,
y2 is-O-or-S,
y3 is a direct bond, or-C (R9R 10) -,
r8 to R10, Q14 and Q15 are the same or different from each other and are each independently hydrogen, deuterium, nitrile, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkyl sulfoxide, substituted or unsubstituted aryl sulfoxide, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amino, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q14 is an integer of 1 to 3,
q15 is an integer of 1 to 4,
when q14 and q15 are each plural, the structures in plural brackets are the same or different from each other,
[ chemical formula f ]
[ chemical formula g ]
[ chemical formula h ]
In the above-mentioned chemical formulas f to h,
u3 to U5 are identical to or different from each other and are each independently a substituted or unsubstituted aryl group,
Q16 to Q21 are the same or different from each other and are each independently hydrogen, deuterium, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amide group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkyl sulfoxide group, substituted or unsubstituted aryl sulfoxide group, substituted or unsubstituted alkenyl group, substituted or unsubstituted silyl group, substituted or unsubstituted boron group, substituted or unsubstituted amine group, substituted or unsubstituted arylphosphine group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group,
q16, q18 and q20 are each integers of 1 to 4,
q17, q19 and q21 are each integers of 1 to 5,
when q16 to q21 are each plural, the structures in plural brackets are the same or different from each other,
in the above-mentioned chemical formulas a to h,is a site bonded to chemical formula 1 through the above L1.
Further, according to one embodiment of the present specification, there is provided an organic light-emitting element including a first electrode, a second electrode provided opposite to the first electrode, and an organic layer including 1 or more layers between the first electrode and the second electrode, wherein 1 or more layers of the organic layer include a heterocyclic compound represented by chemical formula 1.
The heterocyclic compound according to one embodiment of the present specification can be used as a material of an organic layer of an organic light-emitting element, and by using the heterocyclic compound, improvement in efficiency, low driving voltage, and/or improvement in lifetime characteristics of the organic light-emitting element can be achieved.
Drawings
Fig. 1 shows an organic light emitting element 10 according to one embodiment of the present specification.
Fig. 2 shows an organic light emitting element 11 according to another embodiment of the present specification.
Description of symbols
10. 11: organic light-emitting element
20: substrate board
30: first electrode
40: light-emitting layer
50: second electrode
60: hole injection layer
70: hole transport layer
80: electron transport layer
90: electron injection layer
Detailed Description
Hereinafter, the present specification will be described in more detail.
The present specification provides a heterocyclic compound represented by the above chemical formula 1.
In the present specification, when a certain component is indicated as being "included" in a certain portion, unless otherwise stated, this means that other components may be further included, and not excluding other components.
In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where the other member exists between the two members.
In the present specification, examples of the substituents are described below, but are 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 it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means that 1 or 2 or more substituents selected from deuterium, halogen group, nitrile group, nitro group, imide group, amide group, carbonyl group, ester group, hydroxyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkyl sulfoxide group, substituted or unsubstituted aryl sulfoxide group, substituted or unsubstituted alkenyl group, substituted or unsubstituted silyl group, substituted or unsubstituted boron group, substituted or unsubstituted amino group, substituted or unsubstituted aryl phosphine group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group are substituted or are bonded by 2 or more substituents among the substituents exemplified above, or do not have any substituent. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present description of the invention,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 of 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, in the amide group, 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, in the ester group, 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 a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but cycloalkyl having 3 to 30 carbon atoms is preferable, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like are included, but the present invention is not limited thereto.
In the present specification, the above-mentioned alkoxy group may be a straight chain, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specifically, 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-decyloxy, benzyloxy, p-methylbenzyloxy and the like are possible, but not limited thereto.
In the present specification, the amine group may be selected from the group consisting of-NH 2 The alkyl amine group, the N-alkylaryl amine group, the aryl amine group, the N-arylheteroaryl amine group, the N-alkylheteroaryl amine group and the heteroaryl amine group are not particularly limited, but are preferably 1 to 30 in carbon number. Specific examples of the amine group include, but are not limited to, methylamino group, dimethylamino group, ethylamino group, diethylamino group, phenylamine group, naphthylamino group, biphenylamino group, anthracenylamino group, 9-methyl-anthracenylamino group, diphenylamino group, N-phenylnaphthylamino group, xylylamino group, N-phenyltolylamino group, triphenylamino group, N-phenylbiphenylamino group, N-phenylnaphthylamino group, N-biphenylnaphthylamino group, N-naphthylfluorenylamino group, N-phenylphenanthrylamino group, N-biphenylphenanthrenylamino group, N-phenylfluorenylamino group, N-phenylterphenylamino group, N-phenanthrenylfluolamino group, N-biphenylfluorenylamino group and the like.
In the present specification, the N-alkylaryl amine group means an amine group in which an alkyl group and an aryl group are substituted on N of the amine 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 N of the amino group.
In the present specification, the N-alkylheteroaryl amine group means an amine group in which an alkyl group and a heteroaryl group are substituted on N of the amine group.
In the present specification, alkylamino, N-arylalkylamino, alkylthio [ ]Alkylthio), alkylsulfoxide (++>Alkyl groups in the Alkyl sulfoxy) and N-alkylheteroaryl amine groups are the same as those exemplified for the Alkyl groups described above. Specifically, the alkylthio group includes a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group, and the like, and the alkylthio group includes a methanesulfonyl group, an ethylsulfoxide group, a propylsulfoxide group, a butylsulfoxide group, and the like, but is not limited thereto.
In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples thereof include 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 (diphenyl-1-yl) ethen-1-yl, stilbene and styryl, but are not limited thereto.
In the present specification, examples of silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.
In the present specification, the boron group mayfor-BR 100 R 101 R is as described above 100 And R is 101 And each independently may be selected from hydrogen, deuterium, halogen, nitrile, substituted or unsubstituted monocyclic or polycyclic cycloalkyl of 3 to 30 carbon atoms, substituted or unsubstituted straight or branched alkyl of 1 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl of 6 to 30 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic heteroaryl of 2 to 30 carbon atoms.
In the present specification, examples of the phosphine oxide group include, but are not limited to, diphenyl phosphine oxide group, dinaphthyl phosphine oxide group, and the like.
In the present specification, the aryl group is not particularly limited, but is preferably a group having 6 to 30 carbon atoms, and the aryl group may be a single ring or a multiple ring.
In the case where the above 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 phenyl, biphenyl, terphenyl, or the like, but is not limited thereto.
In the case where the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specifically, the polycyclic aryl group may be naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, phenalenyl (phenalenyl), perylenyl,A radical, a fluorenyl radical, etc., but is not limited thereto.
In the present specification, the above fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.
In the case where the above fluorenyl group is substituted, it may be Etc., but is not limited thereto.
In the present specification, the term "adjacent" group means a substituent substituted on an atom directly bonded to an atom substituted with a relevant substituent, a substituent closest to the relevant substituent in a steric structure, or another substituent substituted on an atom substituted with a relevant substituent. For example, 2 substituents substituted in the ortho (ortho) position on the phenyl ring and 2 substituents substituted on the same carbon on the aliphatic ring may be interpreted as "adjacent" groups to each other.
In the present specification, aryloxy group and arylthio group [ ]Aryl-thio-xy) Aryl sulfoxide [ ]Aryl is exemplified by Aryl sulfoxy), N-arylalkylamino, N-arylheteroarylamino, and arylphosphino as described above. Specifically, examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3, 5-dimethyl-phenoxy group, a 2,4, 6-trimethylphenoxy group, a p-t-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthracenyloxy group, a 2-anthracenyloxy group, a 9-anthracenyloxy group, a 1-phenanthrenyloxy group, a 3-phenanthrenyloxy group, a 9-phenanthrenyloxy group, etc., and examples of the arylthio group include a phenylthio group, a 2-methylphenyl thio group, a 4-t-butylphenylthio group, etc., and examples of the arylthio group include a phenylthio group, a p-tolyl sulfoxide group, etc., but are not limited thereto.
In the present specification, as examples of the arylamine group, there are a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamino 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 of the above 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 may be selected from the examples of the aryl groups.
In this specification, heteroaryl groups contain 1 or more non-carbon atoms, i.e., heteroatoms, specifically,the hetero atom 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, the heteroaryl group may be a single ring or multiple rings, and examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo- >Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl) yl, thiazolyl, iso ∈ ->Azolyl, (-) -and (II) radicals>Diazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, as examples of the heteroarylamino group, there are a substituted or unsubstituted mono-heteroarylamino group, a substituted or unsubstituted di-heteroarylamino group, or a substituted or unsubstituted tri-heteroarylamino group. The heteroarylamine group containing 2 or more of the above 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 above heteroaryl amine group may be selected from the examples of the heteroaryl group described above.
In the present specification, examples of heteroaryl groups in the N-arylheteroarylamino group and the N-alkylheteroarylamino group are the same as those described above.
In the present specification, arylene means a group having two bonding sites on an aryl group, i.e., a 2-valent group. The above description of aryl groups may be employed, except that each is a 2-valent group.
In the present specification, heteroaryl means a group having two binding sites on heteroaryl, i.e., a 2-valent group. They may be as described above for heteroaryl groups, except that each is a 2-valent group.
In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In the present specification, the hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic group and an aliphatic group, and may be selected from the examples of cycloalkyl groups and aryl groups, in addition to the non-1-valent groups.
In the present specification, the aromatic ring may be a single ring or multiple rings, and may be selected from the above examples of aryl groups, except for a group having a valence other than 1.
In this specification, a heterocyclic ring contains 1 or more non-carbon atoms, i.e., heteroatoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, se, S and the like. The heterocycle may be a single ring or multiple rings, may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic group and an aliphatic group, and may be selected from the examples of the heteroaryl group and the heterocyclic group, except for a group having a valence other than 1.
According to one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-12.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
[ chemical formulas 1-7]
[ chemical formulas 1-8]
[ chemical formulas 1-9]
[ chemical formulas 1-10]
[ chemical formulas 1-11]
[ chemical formulas 1-12]
In the above chemical formulas 1-1 to 1-12,
l1, L2, ar1, X1 to X3, R1 and R2 are as defined in the above chemical formula 1.
According to one embodiment of the present specification, in the above chemical formula 1, any one of X1 to X3 is N, and the rest is CH.
According to one embodiment of the present specification, in the above chemical formula 1, two of X1 to X3 are N, and the rest are CH.
According to one embodiment of the present specification, in the above chemical formula 1, X1 to X3 are N.
According to one embodiment of the present specification, in the above chemical formula 1, L1 and L2 are the same or different from each other and are each independently a direct bond, or an arylene group.
According to one embodiment of the present specification, in the above chemical formula 1, L1 and L2 are the same or different from each other and are each independently a direct bond, or a phenylene group.
According to one embodiment of the present specification, in the above chemical formula 1, R1 and R2 are the same or different from each other and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
According to one embodiment of the present specification, in the above chemical formula 1, R1 and R2 are the same or different from each other and are each independently aryl or heteroaryl substituted or unsubstituted with aryl.
According to one embodiment of the present specification, in the above chemical formula 1, R1 and R2 are the same or different from each other and are each independently phenyl, biphenyl, naphthyl, or dibenzofuranyl substituted or unsubstituted with aryl.
According to one embodiment of the present specification, in the above chemical formula 1, R1 and R2 are the same or different from each other and are each independently phenyl, biphenyl, naphthyl, or dibenzofuranyl substituted or unsubstituted with phenyl.
According to one embodiment of the present specification, in the above chemical formula a, Q5 and Q6, Q6 and Q7, or Q7 and Q8 are combined with each other to form a substituted or unsubstituted ring.
According to one embodiment of the present specification, in the above chemical formula a, Q5 and Q6, Q6 and Q7, or Q7 and Q8 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to one embodiment of the present specification, in the above chemical formula a, Q5 and Q6, Q6 and Q7, or Q7 and Q8 are combined with each other to form a substituted or unsubstituted benzene ring.
According to one embodiment of the present specification, in the above chemical formula a, Q5 and Q6, Q6 and Q7, or Q7 and Q8 are combined with each other to form a benzene ring.
According to one embodiment of the present specification, the above chemical formula a is represented by any one of the following chemical formulas a-1 to a-5.
[ formula a-1]
[ formula a-2]
[ formula a-3]
[ formula a-4]
[ chemical formula a-5]
In the above formulas a-1 to a-5,
q1 to Q8, R6 and R7 are as defined above for formula a,
q101 is hydrogen, deuterium, nitrile, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkyl sulfoxide, substituted or unsubstituted aryl sulfoxide, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amino, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q101 is an integer of 1 to 4,
when Q101 is plural, plural Q101 are the same or different from each other,
is a site bonded to chemical formula 1 through L1 of chemical formula 1.
According to one embodiment of the present specification, in the above chemical formula a, Q1 to Q8 are hydrogen.
According to one embodiment of the present specification, in the above chemical formula a-2, R6 and R7 are the same or different from each other and are each independently an alkyl group.
According to one embodiment of the present specification, in the above chemical formula a-2, R6 and R7 are methyl groups.
According to one embodiment of the present specification, Q101 is hydrogen in the above formulas a-3 to a-5.
According to one embodiment of the present specification, the above chemical formula b is represented by any one of the following chemical formulas b-1 to b-6.
[ formula b-1]
[ formula b-2]
[ formula b-3]
[ formula b-4]
[ formula b-5]
[ formula b-6]
In the above formulas b-1 to b-6,
u1 is as defined above for formula b.
Q102 is hydrogen, deuterium, nitrile, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkyl sulfoxide, substituted or unsubstituted aryl sulfoxide, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amino, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q102 is an integer from 1 to 4,
when Q102 is plural, plural Q102 are the same or different from each other,
is a site bonded to chemical formula 1 through L1 of chemical formula 1.
According to one embodiment of the present specification, in the above chemical formula b, U1 is aryl substituted or unsubstituted with alkyl or aryl.
According to one embodiment of the present specification, in the above chemical formula b, U1 is phenyl substituted or unsubstituted, naphthyl, biphenyl, or fluorenyl substituted with methyl.
According to one embodiment of the present specification, Q102 is hydrogen in the above formulas b-2 to b-6.
According to one embodiment of the present specification, the above chemical formula c is represented by any one of the following chemical formulas c-1 to c-6.
[ formula c-1]
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[ formula c-2]
[ formula c-3]
[ formula c-4]
[ formula c-5]
[ formula c-6]
In the above formulas c-1 to c-6,
u2, Q11 to Q13, Q11 and Q13 are as defined in the above formula c.
Q103 is hydrogen, deuterium, nitrile, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkyl sulfoxide, substituted or unsubstituted aryl sulfoxide, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amino, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q103 is an integer of 1 to 4,
when Q103 is plural, plural Q103 are the same or different from each other,
is a site bonded to chemical formula 1 through L1 of chemical formula 1.
According to one embodiment of the present specification, Q103 is hydrogen in the above formulas c-1 to c-6.
According to one embodiment of the present specification, in the above formula c, U2 is aryl substituted or unsubstituted with alkyl or aryl.
According to one embodiment of the present specification, in the above chemical formula c, U2 is phenyl substituted or unsubstituted, naphthyl, biphenyl, or fluorenyl substituted with methyl.
According to one embodiment of the present specification, in the above chemical formula c, Q11 to Q13 are the same or different from each other and are each independently hydrogen, a nitrile group, an aryl group, or a heteroaryl group substituted or unsubstituted with an aryl group.
According to one embodiment of the present specification, in the above chemical formula c, Q11 to Q13 are the same or different from each other and are each independently hydrogen, a nitrile group, a phenyl group, a carbazolyl group substituted or unsubstituted with an aryl group, or a dibenzofuranyl group.
According to one embodiment of the present specification, in the above chemical formula c, Q11 to Q13 are the same or different from each other and are each independently hydrogen, a nitrile group, a phenyl group, a carbazolyl group substituted or unsubstituted by a phenyl group, or a dibenzofuranyl group.
According to one embodiment of the present specification, the above chemical formula e is represented by any one of the following chemical formulas e-1 to e-4.
[ formula e-1]
[ chemical formula e-2]
[ chemical formula e-3]
[ chemical formula e-4]
In the above formulas e-1 to e-4,
r9, R10, Q14, Q15, Q14 and Q15 are as defined above for formula e.
According to one embodiment of the present specification, in the above chemical formula d, R8 is aryl.
According to one embodiment of the present specification, in the above chemical formula d, R8 is phenyl.
According to one embodiment of the present specification, in the above chemical formulas d and e-1, R9 and R10 are the same or different from each other and are each independently an alkyl group.
According to one embodiment of the present specification, R9 and R10 are methyl groups in the above chemical formulas d and e-1.
According to one embodiment of the present specification, in the above chemical formulas d and e, Q14 and Q15 are hydrogen.
According to one embodiment of the present specification, in the above chemical formulas f to h, U3 to U5 are the same or different from each other and are each independently an aryl group.
According to one embodiment of the present specification, in the above chemical formulas f to h, U3 to U5 are phenyl groups.
According to one embodiment of the present specification, Q16 to Q21 are hydrogen in the above chemical formulas f to h.
According to one embodiment of the present specification, the above chemical formula 1-1 is selected from the following compounds.
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According to one embodiment of the present specification, the above chemical formula 1-2 is selected from the following compounds.
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According to one embodiment of the present specification, the above chemical formulas 1 to 3 are selected from the following compounds.
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According to one embodiment of the present specification, the above chemical formulas 1 to 4 are selected from the following compounds.
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According to one embodiment of the present specification, the above chemical formulas 1 to 5 are selected from the following compounds.
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According to one embodiment of the present specification, the above chemical formulas 1 to 6 are selected from the following compounds.
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According to one embodiment of the present specification, the above chemical formulas 1 to 7 are selected from the following compounds.
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According to one embodiment of the present specification, the above chemical formulas 1 to 8 are selected from the following compounds.
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According to one embodiment of the present specification, the above chemical formulas 1 to 9 are selected from the following compounds.
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According to one embodiment of the present specification, the above chemical formulas 1 to 10 are selected from the following compounds.
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According to one embodiment of the present specification, the above chemical formulas 1 to 11 are selected from the following compounds.
According to one embodiment of the present specification, the above chemical formulas 1 to 12 are selected from the following compounds.
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According to one embodiment of the present specification, the core structure of the heterocyclic compound represented by the above chemical formula 1 may be manufactured by the following general formula 1, but is not limited thereto.
[ general formula 1]
In the above formula 1, L2, ar1, X1 to X3, R1 and R2 are as defined in the above formula 1, G1 to G3 are the same as or different from each other, and each is independently a halogen group.
According to one embodiment of the present specification, there is provided an organic light-emitting element including a first electrode, a second electrode provided opposite to the first electrode, and at least 1 organic layer provided between the first electrode and the second electrode, wherein at least 1 of the organic layers contains the heterocyclic compound.
According to one embodiment of the present specification, the organic layer of the organic light-emitting element of the present specification may be formed of a single-layer structure or 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, or the like as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and may include a smaller or larger number of organic layers.
For example, the structure of the organic light emitting element of 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 is an exemplary structure of an organic light emitting element according to an embodiment of the present specification, and may further include other organic layers.
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 above is an exemplary structure according to an embodiment of the present specification, and may further include other organic layers.
According to one embodiment of the present specification, the organic layer includes a light-emitting layer including a heterocyclic compound represented by chemical formula 1.
According to one embodiment of the present specification, the organic layer includes a light-emitting layer including a heterocyclic compound represented by chemical formula 1 as a main body of the light-emitting layer.
According to one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or a layer that performs electron injection and transport at the same time, and the electron injection layer, the electron transport layer, or the layer that performs electron injection and transport at the same time includes a heterocyclic compound represented by chemical formula 1.
According to an embodiment of the present specification, 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.
The organic light-emitting element of the present specification can be manufactured by materials and methods known in the art, except that 1 or more of the organic layers contains the heterocyclic compound of the present specification, that is, the heterocyclic compound represented by the above chemical formula 1.
In the case where 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 of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: a first electrode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by a physical vapor deposition method (physical Vapor Deposition, PVD) such as a sputtering method (sputtering) or an electron beam evaporation method (e-beam evaporation), 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 then a substance usable as a second electrode is vapor deposited on the organic layer. In addition to such a 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, the organic layer may be formed not only by a vacuum vapor deposition method but also by a solution coating method in the production of an organic light-emitting element. The solution coating method is, but not limited to, spin coating, dip coating, blade coating, ink jet printing, screen printing, spray coating, roll coating, and the like.
According to one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.
According to another embodiment of the present specification, the first electrode is a cathode, and the second electrode is an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And multi-layer structural materials such as Al and Mg/Ag, but not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: the light-emitting device has a hole transporting capability, a hole injecting effect from an anode, an excellent hole injecting effect for a light-emitting layer or a light-emitting material, prevention of migration of excitons generated in the light-emitting layer to the electron injecting layer or the electron injecting material, and an excellent thin film forming capability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer, but are not limited thereto.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and as a hole-transporting substance, a substance that can receive holes from the anode or the hole-injecting layer and transport the holes to the light-emitting layer, and a substance having a large hole mobility is suitable. Specific examples thereof include an arylamine-based organic substance, a conductive polymer, and a block copolymer having both conjugated and unconjugated portions, but are not limited thereto.
The light-emitting substance of the light-emitting layer is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, and pentacene derivativesExamples of the heterocyclic compound include carbazole derivative, dibenzofuran derivative, and ladder-type furan compoundPyrimidine derivatives, and the like, but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group, Bisindenopyrene (perillanthene), etc., as a styrylamine compound, a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, is substituted or unsubstituted with 1 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but not limited thereto. Further, as the metal complex, there are iridium complex, platinum complex, and the like, but not limited thereto.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and as an electron transporting substance, a substance that can well receive electrons from the cathode and transfer them to the light emitting layer, and a substance having a large electron mobility is suitable. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used together with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium are each accompanied by an aluminum layer or a silver layer.
Above-mentionedThe electron injection layer is a layer that injects electrons from the electrode, and is preferably the following compound: has an electron transporting ability, an electron injecting effect from a cathode, an excellent electron injecting effect to a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from migrating to a hole injecting layer, and has an excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane (Anthraquinone), diphenoquinone, thiopyran dioxide,Azole,/->Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and derivatives, metal complexes, nitrogen-containing 5-membered ring derivatives, and the like thereof, but are not limited thereto.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (2-methyl-8-quinoline) gallium chloride, gallium bis (2-methyl-8-quinoline) (o-cresol), aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol), and the like.
The organic light emitting element of the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
According to one embodiment of the present specification, the heterocyclic compound represented by chemical formula 1 may be contained in an organic solar cell or an organic transistor in addition to an organic light-emitting element.
Hereinafter, for the purpose of specifically describing the present specification, examples will be described in detail. However, the embodiments of the present specification may be modified into various other forms, and the scope of the present specification is not to be construed as being limited to the embodiments described in detail below. The embodiments of the present specification are provided to more fully explain the present specification to one of ordinary skill in the art.
[ reaction type 1]
[ reaction type 2]
[ reaction type 3]
Based on the above-mentioned reaction formulae 1 to 3, compounds A to C and A-1 to C-1 are produced, respectively.
PREPARATION EXAMPLE 1
1) Synthesis of Compound 1-1
After compound a (36.91 g,144.19 mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (35.0 g,131.09 mmol) were completely dissolved in 300ml of tetrahydrofuran in a 1L round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (150 ml) was added, tetrakis (triphenylphosphine) palladium (4.54 g,3.93 mmol) was placed, and then heated and stirred for 6 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 220ml of ethyl acetate to produce 49.66g (85%) of Compound 1-1.
MS[M+H] + ＝444
2) Synthesis of Compound 1
After complete dissolution of compound 1-1 (5.24 g,11.83 mmol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (3.73 g,12.98 mmol) in 180ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (90 ml) was added and tetrakis (triphenylphosphine) palladium (0.12 g,0.24 mmol) was placed in it, followed by heating and stirring for 3 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 120ml of tetrahydrofuran to produce 5.11g (67%) of Compound 1.
MS[M+H] + ＝651
PREPARATION EXAMPLE 2
After complete dissolution of compound 1-1 (5.0 g,11.29 mmol) and (9-phenyl-9H-carbazol-2-yl) boronic acid (3.55 g,12.39 mmol) in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (110 ml) was added and tetrakis (triphenylphosphine) palladium (0.12 g,0.23 mmol) was placed in it and heated under stirring for 3 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 130ml of tetrahydrofuran to produce 5.67g (77%) of compound 2.
MS[M+H] + ＝651
PREPARATION EXAMPLE 3
After complete dissolution of compound 1-1 (5.59 g,12.62 mmol) and dibenzo [ b, d ] furan-2-ylboronic acid (2.94 g,13.88 mmol) in 160ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (80 ml) was added, tetrakis (triphenylphosphine) palladium (0.44 g,0.38 mmol) was placed, followed by heating and stirring for 3 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 180ml of ethyl acetate to produce 5.97g (82%) of Compound 3.
MS[M+H] + ＝576
PREPARATION EXAMPLE 4
After complete dissolution of compound 1-1 (6.32 g,14.27 mmol) and dibenzo [ b, d ] thiophen-2-ylboronic acid (3.58 g,15.69 mmol) in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.49 g,0.43 mmol) was placed in it, followed by heating and stirring for 3 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 160ml of tetrahydrofuran to produce 4.49g (53%) of Compound 4.
MS[M+H] + ＝592
PREPARATION EXAMPLE 5
After complete dissolution of compound 1-1 (6.42 g,14.49 mmol) and (9, 9-dimethyl-10-phenyl-9, 10-dihydroacridin 2-yl) boronic acid (5.24 g,15.94 mmol) in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (110 ml) was added and tetrakis (triphenylphosphine) palladium (0.50 g,0.43 mmol) was placed and then heated and stirred for 8 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 220ml of ethyl acetate to produce 7.11g (71%) of Compound 5.
MS[M+H] + ＝693
PREPARATION EXAMPLE 6
1) Synthesis of Compound 6-1
After compound a (12.35 g,48.25 mmol) and 4- ([ 1,1' -biphenyl ] -4-yl) -6-chloro-2-phenylpyrimidine (15.0 g,43.86 mmol) were completely dissolved in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (110 ml) was added, tetrakis (triphenylphosphine) palladium (1.52 g,1.32 mmol) was placed, and then heated and stirred for 3 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 320ml of ethyl acetate to produce 18.85g (83%) of Compound 6-1.
MS[M+H] + ＝519
2) Synthesis of Compound 6
After complete dissolution of compound 6-1 (9.0 g,17.34 mmol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (5.47 g,19.08 mmol) in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added and tetrakis (triphenylphosphine) palladium (0.60 g,0.52 mmol) was placed in it, followed by heating and stirring for 3 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 160ml of tetrahydrofuran to produce 8.22g (65%) of Compound 6.
MS[M+H] + ＝726
PREPARATION EXAMPLE 7
1) Synthesis of Compound 7-1
After complete dissolution of compound a-1 (30.0 g,103.45 mmol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (32.66 g,113.79 mmol) in 400ml of tetrahydrofuran in a 1L round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (180 ml) was added and tetrakis (triphenylphosphine) palladium (3.59 g,3.10 mmol) was placed in it and heated under stirring for 10 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, the mixture was recrystallized from 320ml of ethyl acetate to yield 35.47g (76%) of Compound 7-1.
MS[M+H] + ＝454
2) Synthesis of Compound 7-2
Under nitrogen atmosphere in a 1L round bottom flaskCompound 7-1 (35.47 g,78.30 mmol), pinacol-diborane (25.85 g,101.79 mmol), potassium acetate (16.44 g,195.75 mmol) were completely dissolved in 1, 4-di-n After 520ml of alkane, heating was performed. After stirring at reflux for 1h, pd (dppf) Cl2 (2.02 g,2.35 mmol) was added and the reaction was then carried out for 8 hours. The temperature was lowered to room temperature and concentrated under reduced pressure, followed by filtration to remove salts. 1, 4-Di->The alkane was recrystallized from 850ml of ethanol to yield 30.07g (70%) of Compound 7-2.
MS[M+H] + ＝546
3) Synthesis of Compound 7
/>
After complete dissolution of compound 7-2 (19.77 g,36.27 mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (7.45 g,27.90 mmol) in tetrahydrofuran 250ml in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added and tetrakis (triphenylphosphine) palladium (0.72 g,0.84 mmol) was placed, followed by stirring with heating for 5 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 320ml of ethyl acetate to produce 15.26g (84%) of Compound 7.
MS[M+H] + ＝651
PREPARATION EXAMPLE 8
After complete dissolution of compound 7-2 (9.96 g,18.27 mmol) and 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (5.44 g,14.06 mmol) in 250ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.36 g,0.42 mmol) was placed, followed by stirring with heating for 3 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 190ml of tetrahydrofuran to produce 8.33g (82%) of Compound 8.
MS[M+H] + ＝727
PREPARATION EXAMPLE 9
After complete dissolution of compound 1-1 (6.64 g,14.99 mmol) and (9-phenyl-9H-carbazol-2-yl) boronic acid (7.07 g,19.49 mmol) in 280ml of tetrahydrofuran in a 1L round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (140 ml) was added and tetrakis (triphenylphosphine) palladium (0.52 g,0.45 mmol) was placed in it and heated and stirred for 5 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 230ml of tetrahydrofuran to produce 6.79g (62%) of Compound 9.
MS[M+H] + ＝727
Production example 10 ]
1) Synthesis of Compound 10-1
After compound B (8.91 g,13.48 mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (8.45 g,31.56 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, tetrakis (triphenylphosphine) palladium (1.09 g,0.95 mmol) was placed, and then heated and stirred for 4 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 220ml of ethyl acetate to produce 7.65g (71%) of Compound 10-1.
MS[M+H] + ＝444
2) Synthesis of Compound 10
After the compound 10-1 (5.52 g,12.46 mmol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (4.65 g,16.20 mmol) were completely dissolved in 260ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (130 ml) was added, tetrakis (triphenylphosphine) palladium (0.43 g,0.37 mmol) was placed and then heated and stirred for 3 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 210ml of tetrahydrofuran to produce 5.66g (70%) of compound 10.
MS[M+H] + ＝651
PREPARATION EXAMPLE 11
1) Synthesis of Compound 11-1
After compound B (5.78 g,22.57 mmol) and 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (6.72 g,17.36 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (100 ml) was added, tetrakis (triphenylphosphine) palladium (0.60 g,0.52 mmol) was placed, and then heated and stirred for 6 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 220ml of ethyl acetate to produce 7.12g (79%) of Compound 11-1.
MS[M+H] + ＝519
2) Synthesis of Compound 11
After the compound 11-1 (7.12 g,13.72 mmol) and (9-phenyl-9H-carbazol-4-yl) boronic acid (5.12 g,17.83 mmol) were completely dissolved in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (110 ml) was added, tetrakis (triphenylphosphine) palladium (0.48 g,0.41 mmol) was placed, followed by stirring with heating for 5 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 230ml of tetrahydrofuran to produce 6.53g (65%) of Compound 11.
MS[M+H] + ＝727
PREPARATION EXAMPLE 12
1) Synthesis of Compound 12-1
After compound C (9.38 g,35.67 mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (7.55 g,29.72 mmol) were completely dissolved in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (110 ml) was added, tetrakis (triphenylphosphine) palladium (1.03 g,0.89 mmol) was placed, and then heated and stirred for 3 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 250ml of ethyl acetate to produce 8.12g (51%) of Compound 12-1.
MS[M+H] + ＝444
2) Synthesis of Compound 12
After the compound 12-1 (8.12 g,18.29 mmol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (6.30 g,21.95 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.63 g,0.55 mmol) was placed, followed by heating and stirring for 4 hours. After the temperature was lowered to normal temperature and concentrated under reduced pressure, recrystallization was performed with 230ml of tetrahydrofuran to produce 7.76g (65%) of compound 12.
MS[M+H] + ＝651
Comparative examples 1 to 1 ]
For the compounds 1 to 12 synthesized in production examples 1 to 12, high-purity sublimation purification was performed by a generally known method, and then a green organic light-emitting element was produced by the following method.
Will be as followsThickness film coated with ITThe glass substrate of O (indium tin oxide) was put into distilled water in which a detergent was dissolved, and washed with ultrasonic waves. At this time, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered 2 times using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was repeated 2 times with distilled water for 10 minutes. After the distilled water washing is finished, ultrasonic washing is carried out by using isopropanol, acetone and methanol solvents in sequence, and the ultrasonic washing is dried and then the ultrasonic washing is conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, using CBP as a host, m-MTDATA (60 nm)/TCTA (80 nm)/CBP+10% Ir (ppy) 3 The order of (300 nm)/BCP (10 n m)/Alq 3 (30 nm)/LiF (1 nm)/Al (200 nm) constituted a light-emitting element, and an organic EL element was produced.
m-MTDATA、TCTA、Ir(ppy) 3 The structures of CBP and BCP are as follows, respectively.
Experimental example 1-1 ]
An organic light-emitting device was produced in the same manner as in comparative example 1-1 except that the compound 1 was used instead of CBP in comparative example 1-1.
Experimental examples 1-2 ]
An organic light-emitting device was produced in the same manner as in comparative example 1-1 except that the compound 2 was used instead of CBP in comparative example 1-1.
Experimental examples 1 to 3
An organic light-emitting device was produced in the same manner as in comparative example 1-1 except that the compound 3 was used instead of CBP in comparative example 1-1.
Experimental examples 1 to 4
An organic light-emitting device was produced in the same manner as in comparative example 1-1 except that the compound 4 was used instead of CBP in comparative example 1-1.
Experimental examples 1 to 5
An organic light-emitting device was produced in the same manner as in comparative example 1-1 except that the compound 5 was used instead of CBP in comparative example 1-1.
Experimental examples 1 to 6
An organic light-emitting device was produced in the same manner as in comparative example 1-1 except that the compound 7 was used instead of CBP in comparative example 1-1.
Experimental examples 1 to 7
An organic light-emitting device was produced in the same manner as in comparative example 1-1 except that the compound 10 was used instead of CBP in comparative example 1-1.
Experimental examples 1 to 8
An organic light-emitting device was produced in the same manner as in comparative example 1-1 except that the compound 12 was used instead of CBP in comparative example 1-1.
Comparative examples 1 to 2
An organic light-emitting device was produced in the same manner as in comparative example 1-1 except that the following compound GH1 was used instead of CBP in comparative example 1-1.
Comparative examples 1 to 3
An organic light-emitting device was produced in the same manner as in comparative example 1-1 except that the following compound GH2 was used instead of CBP in comparative example 1-1.
[GH2]
Comparative examples 1 to 3
An organic light-emitting device was produced in the same manner as in comparative example 1-1 except that the following compound GH3 was used instead of CBP in comparative example 1-1.
[GH3]
When a current was applied to the organic light emitting elements fabricated in experimental examples 1-1 to 1-8 and comparative examples 1-1 to 1-4, voltage, efficiency, emission peak and lifetime were measured, and the results thereof are shown in table 1. T95 refers to the time required for the luminance to decrease to (5000 nit) 95% of the original luminance.
TABLE 1
As a result of the experiment, it was confirmed that the green organic light emitting elements of the experimental examples 1-1 to 1-8 using the heterocyclic compound represented by chemical formula 1 according to one embodiment of the present specification as a host substance of the light emitting layer exhibited more excellent performance in terms of current efficiency and driving voltage, as compared to the organic light emitting elements manufactured using the comparative example 1-1 of the conventional CBP and the compound of the comparative example 1-2 in which the substituents are attached to the 9 and 10 positions of the phenanthrene group as the host substance. The measured T95 life is also 15 to 30 percent higher.
Further, the organic light-emitting elements of examples 1-1 to 1-8 obtained excellent effects that the efficiency was 10% or more as compared with comparative examples 1-3 and 1-4, which used a compound having a carbazolyl group substituted with a phenyl group bonded to a phenanthrylene group at the 4-position as a host substance of the organic light-emitting element.
Comparative example 2-1 ]
Will be as followsGlass substrates coated with ITO (indium tin oxide) in thin films were put into distilled water in which a detergent was dissolved, and washed with ultrasonic waves. In this case, a product of fei-hill (Fischer co.) was used as the detergent, and a product of millbox (Millipore co.) produced Filter (Filter) and distilled water after 2 times filtration. After washing the ITO for 30 minutes, ultrasonic washing was repeated 2 times with distilled water for 10 minutes. After the distilled water washing is finished, ultrasonic washing is carried out by using isopropanol, acetone and methanol solvents in sequence, and the ultrasonic washing is dried and then the ultrasonic washing is conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, toHexanitrile hexaazatriphenylene (hexanitrile hexaazatriphenylene, HAT) of the following chemical formula was thermally vacuum evaporated to form a hole injection layer.
Vacuum vapor-depositing the following compound HT1, N4, N4, N4', N4' -tetrakis ([ 1,1' -biphenyl), as a hole-transporting substance, on the hole-injecting layer]-4-yl) - [1,1' -biphenyl]-4,4' -diamineA hole transport layer is formed. />
Next, the hole transport layer is coated withThe following compound EB1 was vacuum-deposited to form an electron blocking layer.
Then, on the electron blocking layerThe following BH and BD were vacuum deposited at a weight ratio of 25:1 to form a light-emitting layer.
On the light-emitting layer, 1:1 weight ratio vacuum evaporating the above-mentioned compound ET1 and the above-mentioned compound LiQ (lithium hydroxyquinoline, lithium Quinolate) toForm an electron injection and transport layer. Sequentially by +.>Thickness evaporation of lithium fluoride (LiF), in +.>Aluminum is deposited in thickness to form a cathode. />
In the process, the vapor deposition speed of the organic matters is maintainedLithium fluoride maintenance of cathode>Aluminum maintenance->Is to maintain the vacuum degree at 2X 10 during vapor deposition -7 ～5×10 -6 And (3) torr, thereby manufacturing the organic light-emitting element.
Experimental example 2-1 ]
Experiments were performed in the same manner as in comparative example 2-1 except that compound 1 was used instead of compound ET 1.
Experimental example 2-2 ]
Experiments were performed in the same manner as in comparative example 2-1 except that compound 2 was used instead of compound ET 1.
Experimental examples 2 to 3
Experiments were performed in the same manner as in comparative example 2-1 except that compound 5 was used instead of compound ET 1.
Experimental examples 2 to 4
Experiments were performed in the same manner as in comparative example 2-1 except that compound 6 was used instead of compound ET 1.
Experimental examples 2 to 5
Experiments were performed in the same manner as in comparative example 2-1 except that compound 7 was used instead of compound ET 1.
Experimental examples 2 to 6
Experiments were performed in the same manner as in comparative example 2-1 except that compound 8 was used instead of compound ET 1.
Experimental examples 2 to 7
Experiments were performed in the same manner as in comparative example 2-1 except that compound 9 was used instead of compound ET 1.
Experimental examples 2 to 8
Experiments were performed in the same manner as in comparative example 2-1 except that compound 10 was used instead of compound ET 1.
Experimental examples 2 to 9
Experiments were performed in the same manner as in comparative example 2-1 except that compound 11 was used instead of compound ET 1.
Experimental examples 2 to 10
Experiments were performed in the same manner as in comparative example 2-1 except that compound 12 was used instead of compound ET 1.
Comparative examples 2 to 2]
An organic light-emitting device was produced in the same manner as in comparative example 2-1 except that the following compound ET2 was used instead of the compound ET1 in comparative example 2-1.
Comparative examples 2 to 2]
An organic light-emitting device was produced in the same manner as in comparative example 2-1 except that the following compound ET3 was used instead of the compound ET1 in comparative example 2-1.
[ET3]
The results of table 2 were obtained when current was applied to the organic light emitting elements fabricated from experimental examples 2-1 to 2-10 and comparative examples 2-1 to 2-3.
TABLE 2
As a result of the experiment, it was confirmed that the organic light emitting elements of experimental examples 2-1 to 2-10 using the heterocyclic compound represented by chemical formula 1 according to one embodiment of the present specification as an electron injection and transport layer exhibited more excellent performance in terms of current efficiency, driving voltage, as compared to the organic light emitting elements of comparative example 2-1 and comparative example 2-2 having substituents at the 9 and 10 positions of phenanthrene group. In addition, T95 life is greatly increased.
Further, the organic light-emitting elements of examples 2-1 to 2-10 obtained excellent results that were 15% or more higher than those of comparative examples 2-3 using a compound having a phenyl-substituted carbazolyl group bonded to a phenanthrylene group at the 4-position as an electron injection and transport layer material of the organic light-emitting element.
While the preferred embodiments of the present invention (green light emitting layer, electron injection and transport layer) have been described above, the present invention is not limited thereto, and can be implemented by various modifications within the scope of the present invention as claimed and the scope of the specific embodiments of the present invention, and the present invention is also within the scope of the present invention.
The invention also includes the following embodiments:
embodiment 1. A heterocyclic compound represented by the following chemical formula 1:
chemical formula 1
In the above-mentioned chemical formula 1,
l1 and L2 are identical or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
x1 is N or CR3, X2 is N or CR4, X3 is N or CR5,
at least one of X1 to X3 is N,
r1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, nitrile, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkyl sulfoxide, substituted or unsubstituted aryl sulfoxide, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amino, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
Ar1 is a group represented by any one of the following formulas a to h,
chemical formula a
In the chemical formula a, in which the amino acid is represented by the formula a,
y1 is a direct bond, or-C (R6R 7) -,
q1 to Q8 are the same or different from each other and are each independently hydrogen, deuterium, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amide group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkyl sulfoxide group, substituted or unsubstituted aryl sulfoxide group, substituted or unsubstituted alkenyl group, substituted or unsubstituted silyl group, substituted or unsubstituted boron group, substituted or unsubstituted amine group, substituted or unsubstituted arylphosphine group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group, or groups adjacent to each other may be combined with each other to form a substituted or unsubstituted ring,
chemical formula b
In the chemical formula b,
u1 is a substituted or unsubstituted aryl group,
q9 and Q10 are hydrogen or may combine with each other to form a substituted or unsubstituted ring,
q9 is an integer of 1 to 3,
q10 is an integer of 1 to 4,
when q9 and q10 are each plural, the structures in plural brackets are the same or different from each other,
chemical formula c
In the chemical formula c, the chemical formula,
u2 is a substituted or unsubstituted aryl group,
q11 to Q13 are the same or different from each other and are each independently hydrogen, deuterium, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amide group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkyl sulfoxide group, substituted or unsubstituted aryl sulfoxide group, substituted or unsubstituted alkenyl group, substituted or unsubstituted silyl group, substituted or unsubstituted boron group, substituted or unsubstituted amine group, substituted or unsubstituted arylphosphine group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group, or groups adjacent to each other may be combined with each other to form a substituted or unsubstituted ring,
q11 is either 1 or 2 and,
q13 is an integer of 1 to 4,
when q11 and q13 are each plural, the structures in plural brackets are the same or different from each other,
Chemical formula d
Chemical formula e
In the chemical formulas d and e described above,
y2 is-O-or-S,
y3 is a direct bond, or-C (R9R 10) -,
r8 to R10, Q14 and Q15 are the same or different from each other and are each independently hydrogen, deuterium, nitrile, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkyl sulfoxide, substituted or unsubstituted aryl sulfoxide, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amino, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q14 is an integer of 1 to 3,
q15 is an integer of 1 to 4,
when q14 and q15 are each plural, the structures in plural brackets are the same or different from each other,
chemical formula f
Chemical formula g
Chemical formula h
In the chemical formulas f to h described above,
u3 to U5 are identical to or different from each other and are each independently a substituted or unsubstituted aryl group,
Q16 to Q21 are the same or different from each other and are each independently hydrogen, deuterium, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amide group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkyl sulfoxide group, substituted or unsubstituted aryl sulfoxide group, substituted or unsubstituted alkenyl group, substituted or unsubstituted silyl group, substituted or unsubstituted boron group, substituted or unsubstituted amine group, substituted or unsubstituted arylphosphine group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group,
q16, q18 and q20 are each integers of 1 to 4,
q17, q19 and q21 are each integers of 1 to 5,
when q16 to q21 are each plural, the structures in plural brackets are the same or different from each other,
in the chemical formulas a to h described above,is a site bonded to chemical formula 1 by the L1.
Embodiment 2. The heterocyclic compound according to embodiment 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-12:
Chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1-3
Chemical formulas 1-4
Chemical formulas 1-5
Chemical formulas 1-6
Chemical formulas 1-7
Chemical formulas 1-8
Chemical formulas 1-9
Chemical formulas 1-10
Chemical formulas 1-11
Chemical formulas 1-12
In the chemical formulas 1-1 to 1-12,
l1, L2, ar1, X1 to X3, R1 and R2 are as defined in the chemical formula 1.
Embodiment 3. The heterocyclic compound according to embodiment 1, wherein the chemical formula a is represented by any one of the following chemical formulas a-1 to a-5:
formula a-1
Formula a-2
Formula a-3
/>
Formula a-4
Formula a-5
In the chemical formulas a-1 to a-5,
q1 to Q8, R6 and R7 are as defined for formula a,
q101 is hydrogen, deuterium, nitrile, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkyl sulfoxide, substituted or unsubstituted aryl sulfoxide, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amino, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q101 is an integer of 1 to 4,
when Q101 is plural, plural Q101 are the same or different from each other,
to be connected with L1 of the chemical formula 1The binding site of chemical formula 1.
Embodiment 4. The heterocyclic compound according to embodiment 1, wherein the chemical formula b is represented by any one of the following chemical formulas b-1 to b-6:
formula b-1
Formula b-2
Formula b-3
Formula b-4
Formula b-5
Formula b-6
In the chemical formulas b-1 to b-6,
u1 is as defined for formula b,
q102 is hydrogen, deuterium, nitrile, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkyl sulfoxide, substituted or unsubstituted aryl sulfoxide, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amino, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q102 is an integer from 1 to 4,
when Q102 is plural, plural Q102 are the same or different from each other,
is a site bonded to chemical formula 1 by L1 of chemical formula 1.
Embodiment 5. The heterocyclic compound according to embodiment 1, wherein the chemical formula c is represented by any one of the following chemical formulas c-1 to c-6:
formula c-1
Formula c-2
Formula c-3
Formula c-4
Formula c-5
Formula c-6
In the chemical formulas c-1 to c-6,
u2, Q11 to Q13, Q11 and Q13 are as defined for formula c,
q103 is hydrogen, deuterium, nitrile, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkyl sulfoxide, substituted or unsubstituted aryl sulfoxide, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amino, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q103 is an integer of 1 to 4,
when Q103 is plural, plural Q103 are the same or different from each other,
is a site bonded to chemical formula 1 by L1 of chemical formula 1.
Embodiment 6. The heterocyclic compound according to embodiment 1, wherein the chemical formula e is represented by any one of the following chemical formulas e-1 to e-4:
chemical formula e-1
Chemical formula e-2
Chemical formula e-3
Chemical formula e-4
In the chemical formulas e-1 to e-4,
r9, R10, Q14, Q15, Q14 and Q15 are as defined for formula e.
Embodiment 7. The heterocyclic compound according to embodiment 1, wherein R1 and R2 are the same or different from each other and are each independently aryl or heteroaryl substituted or unsubstituted with aryl.
Embodiment 8. The heterocyclic compound according to embodiment 1, wherein the chemical formula 1 is selected from the specific compounds selected from chemical formulas 1-1 to 1-12 above.
Embodiment 9. An organic light-emitting element comprising a first electrode, a second electrode provided opposite to the first electrode, and at least 1 organic layer provided between the first electrode and the second electrode, wherein at least 1 of the organic layers contains the heterocyclic compound according to any one of embodiments 1 to 8.
Embodiment 10. The organic light-emitting element according to embodiment 9, wherein the organic layer comprises a light-emitting layer comprising the heterocyclic compound.
Embodiment 11. The organic light-emitting element according to embodiment 9, wherein the organic layer comprises a light-emitting layer comprising the heterocyclic compound as a host of the light-emitting layer.
Embodiment 12. The organic light-emitting element according to embodiment 9, wherein the organic layer comprises an electron injection layer, an electron transport layer, or a layer that performs electron injection and transport simultaneously, the electron injection layer, the electron transport layer, or the layer that performs electron injection and transport simultaneously comprising the heterocyclic compound.

Claims (6)

1. A heterocyclic compound represented by the following chemical formulas 1 to 9:
chemical formulas 1-9
In the chemical formulas 1 to 9 described above,
l1 and L2 are a direct bond,
x1 is N or CR3, X2 is N or CR4, X3 is N or CR5,
at least one of X1 to X3 is N,
r1 and R2 are the same or different from each other and are each independently an unsubstituted aryl group having 6 to 30 carbon atoms,
r3 to R5 are identical or different from each other and are each independently hydrogen or deuterium,
ar1 is a group represented by any one of the following formulas a-1, b-1, c, e-3 and e-4,
Formula a-1
In the chemical formula a-1 described above,
q1 to Q8 are the same as or different from each other and are each independently hydrogen or deuterium,
formula b-1
In the chemical formula b-1, the amino acid,
u1 is an unsubstituted aryl group having 6 to 30 carbon atoms,
chemical formula c
In the chemical formula c, the chemical formula,
u2 is an unsubstituted aryl group having 6 to 30 carbon atoms,
q11 to Q13 are the same as or different from each other and are each independently hydrogen or deuterium,
q11 is either 1 or 2 and,
q13 is an integer of 1 to 4,
when q11 and q13 are each plural, the structures in plural brackets are the same or different from each other, formula e-3
Chemical formula e-4
In the chemical formulas e-3 and e-4,
q14 and Q15 are the same or different from each other and are each independently hydrogen or deuterium,
q14 is an integer of 1 to 3,
q15 is an integer of 1 to 4,
when q14 and q15 are each plural, the structures in plural brackets are the same or different from each other, and in the chemical formulas a-1, b-1, c, e-3 and e-4,is a site bonded to chemical formulas 1 to 9 through the L1.
2. The heterocyclic compound according to claim 1, wherein the chemical formulas 1 to 9 are selected from the following compounds:
3. an organic light-emitting element comprising a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the heterocyclic compound according to claim 1 or 2.
4. The organic light-emitting element according to claim 3, wherein the organic layer comprises a light-emitting layer comprising the heterocyclic compound.
5. The organic light-emitting element according to claim 3, wherein the organic layer comprises a light-emitting layer comprising the heterocyclic compound as a host of the light-emitting layer.
6. The organic light-emitting element according to claim 3, wherein the organic layer comprises an electron injection layer, an electron transport layer, or a layer which performs electron injection and transport simultaneously, the electron injection layer, the electron transport layer, or the layer which performs electron injection and transport simultaneously comprising the heterocyclic compound.
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