CN111386262B - Heterocyclic compound and organic light-emitting device comprising same - Google Patents

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

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CN111386262B
CN111386262B CN201980005880.2A CN201980005880A CN111386262B CN 111386262 B CN111386262 B CN 111386262B CN 201980005880 A CN201980005880 A CN 201980005880A CN 111386262 B CN111386262 B CN 111386262B
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CN111386262A (en
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金振珠
洪玩杓
尹洪植
姜儒真
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LG Chem Ltd
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Abstract

The present specification relates to a heterocyclic compound of chemical formula 1 and an organic light-emitting device including the same.

Description

Heterocyclic compound and organic light-emitting device comprising same
Technical Field
The present invention claims priority from korean patent application No. 10-2018-0033703, filed to the korean patent office on 3/23 of 2018, the entire contents of which are incorporated herein.
The present specification relates to heterocyclic compounds and organic light-emitting devices including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.
There is a continuing need to develop new materials for use in organic light emitting devices as described above.
Disclosure of Invention
Technical problem
The present specification provides heterocyclic compounds and organic light-emitting devices comprising the same.
Solution to the problem
An embodiment of the present specification provides a heterocyclic compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
any one of G1 and G2 is-L2-Ar 2, the balance is hydrogen,
l1 and L2 are the same or different from each other and are each independently a direct bond, or a substituted or unsubstituted arylene group,
ar1 and Ar2 are each, independently of one another, an Electron Donating Group (EDG) or an Electron Withdrawing Group (EWG),
r1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, nitro, hydroxy, amido, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthioalkylthioxy group), substituted or unsubstituted arylthio (++>arylthio group), substituted or unsubstituted alkylsulfonylalkylsulfoxy group), substituted or unsubstituted arylsulfonyl (++>arylsulfoxy group), a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl phosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,
m and n are each an integer of 1 to 4,
when m is 2 or more, 2 or more of R1 s are the same or different from each other,
when n is 2 or more, 2 or more of R2 are the same or different from each other.
In addition, another embodiment of the present specification provides an organic light emitting device, including: the organic light-emitting device includes a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains the heterocyclic compound.
Effects of the invention
According to an embodiment of the present specification, the heterocyclic compound represented by the above chemical formula 1 is a bipolar (ambipolar) compound having substituents of both n-type (electron withdrawing group (EWG)) and p-type (electron donating group (E DG)) in one molecule, and thus, an organic light emitting device including the same has characteristics of low voltage, high efficiency, and long lifetime.
Drawings
Fig. 1 illustrates an organic light emitting device 10 according to an embodiment of the present specification.
Fig. 2 illustrates an organic light emitting device 11 according to another embodiment of the present specification.
[ description of the symbols ]
10. 11: organic light emitting device
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: an electron injection layer.
Detailed Description
The present specification will be described in more detail below.
The present specification provides a heterocyclic compound represented by the above chemical formula 1.
Specifically, although a spiro structure composed of only carbon atoms may induce an increase in driving voltage due to steric hindrance to prevent electron transfer between molecules, a spiro structure containing heteroatoms including sulfur atoms may be expected to have a lower driving voltage as shown in one embodiment of the present specification. Further, the above chemical formula 1 is a bipolar (ambipolar) compound having substituents of both n-type (electron withdrawing group (EWG)) and p-type (electron donating group (EDG)) in one molecule, and thus, an organic light emitting device including the same as an organic layer exhibits low voltage, high efficiency, and long lifetime by appropriately adjusting electron migration in and between molecules.
In the present specification, when a certain component is indicated as being "included" in a certain portion, unless otherwise stated, it means that other components may be further included, and not excluded.
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 another member exists between the two members.
In the present specification, examples of 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 substituted with 1 or 2 or more substituents selected from deuterium, halogen group, cyano, nitro, 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 alkylsulfonyl group, substituted or unsubstituted arylsulfonyl 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, and substituted or unsubstituted heteroaryl group, or a substituent bonded with 2 or more substituents among the above-exemplified substituents, or does 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 of attachment to other substituents or binding sites.
In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.
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 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 a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamine group, a naphthylamino group, a biphenylamino group, an anthracenylamino group, a 9-methylanthracenylamine group, a diphenylamino group, a xylylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrenylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-biphenylfluorenylamino group, and the like, but are not limited thereto.
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, examples of the alkylamino group include a substituted or unsubstituted monoalkylamino group and a substituted or unsubstituted dialkylamino group. The alkyl group in the above-mentioned alkylamino group may be a linear or branched alkyl group. The alkylamino group containing 2 or more of the above-mentioned alkyl groups may contain a linear alkyl group, a branched alkyl group, or may contain both a linear alkyl group and a branched alkyl group. For example, the alkyl group in the above-mentioned alkylamino group may be selected from the examples of the alkyl group described above.
In the present specification, the alkyl group in the N-alkylaryl amine group, alkylthio group, alkylsulfonyl group, N-alkylheteroaryl amine group is the same as exemplified for the alkyl group 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 alkylsulfonyl group includes a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl 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-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group may be-BR 100 R 101 R is as described above 100 And R is 101 The same or different may each be independently selected from hydrogen, deuterium, a halogen group, cyano, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
In the present specification, the phosphine oxide group specifically includes an alkylphosphine oxide group, an arylphosphine oxide group, and the like, and more specifically includes a diphenylphosphine oxide group, a dinaphthyl phosphine oxide group, and the like, but is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be 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, triphenylene, pyrenyl, phenalenyl, perylenyl,A group, a fluorenyl group, 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. However, the present invention is not limited thereto.
In this specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on the atom substituted by the substituent. For example, 2 substituents substituted in the benzene ring at the ortho (ortho) position and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
In the present specification, the aryl group in the aryloxy group, arylthio group, arylsulfonyl group, N-arylalkylamino group, N-arylheteroarylamino group, and arylphosphino group is the same as exemplified for the aryl group described above. Specifically, examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3, 5-dimethylphenyloxy group, a 2,4, 6-trimethylphenoxy group, a p-tert-butylphenyloxy group, a 3-biphenylyloxy group, a 4-biphenylyloxy 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, and the like, and examples of the arylthio group include a phenylthio group, a 2-methylphenylthio group, a 4-tert-butylphenylthio group, and the like, and examples of the arylsulfonyl group include a phenylsulfonyl group, a p-toluenesulfonyl group, and the like, but are not limited thereto.
In the present specification, as examples of the arylamine group, there are substituted or unsubstituted monoarylamine groups, or substituted or unsubstituted diarylamino groups. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing 2 or more aryl groups described above may contain a monocyclic aryl group, a polycyclic aryl group, or may contain 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 group described above.
In this specification, a heteroaryl group 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 number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -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, phenanthridinyl (++>phenanthrine), phenanthrolineA phenyl group (phenanthrine), an iso-group (L)>Oxazolyl, thiadiazolyl, 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, or a substituted or unsubstituted di-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 may contain 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 heteroaryl groups 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 that there are 2 positions where aryl is bonded, i.e., a 2-valent group. These are not limited to the 2-valent groups, and the above description of the aryl groups may be applied.
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, except for the 1-valent groups.
In the present specification, the aromatic ring may be a single ring or a multiple ring, and may be selected from the above examples of aryl groups, except for 1.
In this specification, a heterocyclic ring contains 1 or more non-carbon atoms, that is, 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 a multiple ring, may be an aromatic, aliphatic, or an aromatic and aliphatic condensed ring, and may be selected from the examples of the heteroaryl group and the heterocyclic group, except for the 1-valent one.
In the present specification, an electron donating group (EDG: electron donative group) is generally a substituent having a negative charge or an unshared electron pair, and is a group that donates electrons to a portion having a positive charge or lacking an electron pair. In addition, the electron donating group in this specification includes a substituent capable of transmitting electrons (excited electrons) to an electron withdrawing group having a large electronegativity because of the abundant electron-retaining property of the molecule itself when light is received in a state of being mixed with the electron withdrawing group even if the substituent does not have a negative charge or an unshared electron pair.
In the present specification, an electron withdrawing group (EWG: electron withdrawing group) refers to a generic term for a substituent that receives an electron from an electron donating group.
According to an embodiment of the present specification, the above chemical formula 1 is represented by the following chemical formula 1-1 or 1-2.
[ chemical formula 1-1]
[ chemical formulas 1-2]
In the above chemical formulas 1-1 and 1-2,
l1, L2, ar1, ar2, R1, R2, m and n are as defined in the above chemical formula 1.
According to one embodiment of the present specification, in the above chemical formula 1, R1 is hydrogen.
According to one embodiment of the present specification, in the above chemical formula 1, R2 is hydrogen.
According to an embodiment of the present specification, the above-mentioned L1 and L2 are the same or different from each other, and each is independently a direct bond or arylene group.
According to an embodiment of the present specification, the above-mentioned L1 and L2 are the same or different from each other, and each is independently a direct bond or a phenylene group.
According to an embodiment of the present disclosure, L1 is a direct bond.
According to one embodiment of the present specification, L1 is phenylene.
According to an embodiment of the present disclosure, the L2 is a direct bond.
According to an embodiment of the present specification, the L2 is phenylene.
According to an embodiment of the present disclosure, ar1 is an Electron Donating Group (EDG).
According to an embodiment of the present disclosure, ar2 is an Electron Withdrawing Group (EWG).
According to an embodiment of the present disclosure, ar1 is an Electron Withdrawing Group (EWG).
According to an embodiment of the present disclosure, ar2 is an Electron Donating Group (EDG).
According to an embodiment of the present specification, the Ar1 and Ar2 are different from each other, the Ar1 is an Electron Donating Group (EDG), and the Ar2 is an Electron Withdrawing Group (EWG).
According to an embodiment of the present specification, the Ar1 and Ar2 are different from each other, the Ar1 is an Electron Withdrawing Group (EWG), and the Ar2 is an Electron Donating Group (EDG).
According to an embodiment of the present specification, the Electron Donating Group (EDG) is selected from a substituted or unsubstituted indolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted hexahydropyridoquinolinyl group, and a substituted or unsubstituted silyl group.
According to an embodiment of the present specification, the Electron Donating Group (EDG) is selected from the group consisting of a carbazolyl group substituted or unsubstituted with an aryl group, an indolocarbazolyl group substituted or unsubstituted with an aryl group, a hexahydropyridoquinolinyl group, and a silyl group substituted or unsubstituted with an aryl group.
According to an embodiment of the present specification, the Electron Donating Group (EDG) is selected from indolyl, carbazolyl substituted or unsubstituted with phenyl, indolocarbazolyl substituted or unsubstituted with phenyl, hexahydropyridoquinolinyl, and triphenylsilyl.
According to an embodiment of the present specification, the Electron Donating Group (EDG) is selected from indolyl, phenyl-substituted or unsubstituted carbazolyl, phenyl-substituted indolocarbazolyl, hexahydropyridoquinolinyl, and triphenylsilyl.
According to an embodiment of the present specification, the Electron Donating Group (EDG) is selected from the groups represented by the following chemical formulas a-1 to a-8, but is not limited thereto.
[ formula A-1]
[ formula A-2]
[ formula A-3]
[ formula A-4]
[ chemical formula A-5]
[ chemical formula A-6]
[ chemical formula A-7]
[ chemical formula A-8]
In the above formulas a-1 to a-8,
q1 to Q14 and Q101 to Q103 described above are the same or different from each other and each is independently hydrogen, deuterium, a halogen group, cyano, 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 alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amino, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q1, q4 and q6 are each integers of 1 to 6,
q2 is an integer of 1 to 8,
q3 is an integer of 1 to 7,
q5 and q7 are each an integer of 1 to 4,
q10 is 1 or 2 and is preferably selected from the group consisting of,
q11 is an integer of 1 to 12,
q12 to q14 are each an integer of 1 to 5,
when q1 to q7 and q11 to q14 are each 2 or more, the structures in parentheses of 2 or more are the same or different from each other,
when Q10 is 2, the 2Q 10 are the same or different from each other,
refers to a portion bonded to the above chemical formula 1.
According to an embodiment of the present specification, the Electron Donating Group (EDG) is selected from groups represented by the following structures, but is not limited thereto.
In the above-mentioned structure, the first and second heat exchangers,
the definition of Q8, Q9 and Q101 to Q103 is the same as that described above,is a part bonded to the above chemical formula 1.
According to an embodiment of the present specification, the Electron Donating Group (EDG) is selected from groups represented by the following structures, but is not limited thereto.
In the above-mentioned structure, the first and second heat exchangers,
is a part bonded to the above chemical formula 1.
According to an embodiment of the present specification, the Electron Withdrawing Group (EWG) is selected from cyano groups, aryl groups substituted with 1 or more cyano groups, substituted or unsubstituted N-containing monocyclic heteroaryl groups, substituted or unsubstituted 3-ring heteroaryl groups containing O or S, and substituted or unsubstituted 3-ring heteroaryl groups containing 2 or more of N, O and S.
According to an embodiment of the present specification, the Electron Withdrawing Group (EWG) is selected from cyano groups, aryl groups substituted with 1 or more cyano groups, N-containing monocyclic heteroaryl groups substituted or unsubstituted with aryl groups, 3-ring heteroaryl groups substituted or unsubstituted with cyano groups including O or S, and 3-ring heteroaryl groups substituted or unsubstituted with cyano groups including 2 or more of N, O and S.
According to an embodiment of the present specification, the Electron Withdrawing Group (EWG) is selected from cyano groups, phenyl groups substituted with 1 or more cyano groups, pyridyl groups substituted with aryl groups, pyrimidinyl groups substituted with aryl groups, triazinyl groups substituted with aryl groups, dibenzofuranyl groups substituted with cyano groups or unsubstituted dibenzothiophenyl groups substituted with cyano groups.
According to an embodiment of the present specification, the above Electron Withdrawing Group (EWG) is selected from cyano, phenyl substituted with 1 or more cyano groups, pyridyl substituted with 1 or more substituents selected from phenyl and biphenyl, pyrimidinyl substituted with 1 or more substituents selected from phenyl and biphenyl, triazinyl substituted with 1 or more substituents selected from phenyl and biphenyl, dibenzofuranyl substituted or unsubstituted with cyano groups, and dibenzothienyl substituted or unsubstituted with cyano groups.
According to an embodiment of the present specification, the above Electron Withdrawing Group (EWG) is selected from the groups represented by the following chemical formulas B-1 to B-4, but is not limited thereto.
[ chemical formula B-1]
[ chemical formula B-2]
[ chemical formula B-3]
[ chemical formula B-4]
In the above formulas B-1 to B-4,
at least one of X1 to X3 is N, the rest is CH,
X4 is N or CT4, X5 is N or CT5, X6 is N or CT6, X7 is N or CT7, Y1 is O or S,
t1 to T7 are identical to or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, 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 alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted arylphosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q is an integer of 1 to 5,
t3 is an integer of 1 to 3,
when T3 is 2 or more, T3 of 2 or more are the same or different from each other,
is a part bonded to the above chemical formula 1.
According to an embodiment of the present specification, the Electron Withdrawing Group (EWG) is selected from groups represented by the following structures, but is not limited thereto.
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In the above-described structure, the first and second heat exchangers,
q, T1, T2 and T4 to T7 are as defined above,
is a part bonded to the above chemical formula 1.
According to one embodiment of the present disclosure, q is 1 or 2.
According to an embodiment of the present specification, T1 and T2 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group.
According to an embodiment of the present specification, T1 and T2 are the same or different from each other, and each is independently an aryl group.
According to an embodiment of the present specification, T1 and T2 are the same or different from each other, and each is independently a phenyl group or a biphenyl group.
According to one embodiment of the present disclosure, T1 and T2 are phenyl groups.
According to one embodiment of the present specification, T1 is phenyl, and T2 is biphenyl.
According to one embodiment of the present specification, T1 is biphenyl, and T2 is phenyl.
According to one embodiment of the present specification, T1 and T2 are biphenyl groups.
According to an embodiment of the present specification, T4 to T7 are the same as or different from each other, and each is independently hydrogen or cyano.
According to an embodiment of the present specification, T4 to T7 are hydrogen.
According to an embodiment of the present specification, at least one of T4 to T7 is cyano, and the rest is hydrogen.
According to an embodiment of the present specification, the Electron Withdrawing Group (EWG) is selected from groups represented by the following structures, but is not limited thereto.
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According to one embodiment of the present specification, the above chemical formula 1 is selected from the following compounds.
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The present specification provides an organic light-emitting device comprising the heterocyclic compound described above.
According to an embodiment of the present specification, an organic light emitting device includes: a first electrode, a second electrode provided opposite to the first electrode, and at least one organic layer provided between the first electrode and the second electrode, wherein one or more of the organic layers contains a heterocyclic compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present specification may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a hole adjustment layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron adjustment layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
For example, the structure of the organic light emitting device 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 device 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 device 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 device 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 is an exemplary structure according to an embodiment of the present disclosure, and may further include other organic layers. The compound represented by the above chemical formula 1 may be included in the above hole injection layer 60, hole transport layer 70, light emitting layer 40, electron transport layer 80, electron injection layer 90, preferably, may be included in the light emitting layer.
According to one embodiment of the present disclosure, 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 host of the light-emitting layer.
According to an embodiment of the present specification, the light emitting layer may include a heterocyclic compound represented by chemical formula 1 as a host of the light emitting layer, and may further include a dopant.
According to an embodiment of the present specification, the light-emitting layer may include a heterocyclic compound represented by chemical formula 1 as a main body of the light-emitting layer, and may further include a delayed fluorescent substance.
According to an embodiment of the present disclosure, the light-emitting layer may use a metal complex such as an iridium-based dopant as a dopant.
According to an embodiment of the present specification, the light emitting layer may include a host and a dopant in a weight ratio of 99:1 to 30:70.
According to an 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 one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes a heterocyclic compound represented by chemical formula 1.
According to an embodiment of the present specification, the organic layer includes an electron modulation layer including a heterocyclic compound represented by chemical formula 1.
According to one embodiment of the present specification, the organic layer includes an organic layer including a heterocyclic compound represented by the chemical formula 1, and further includes a hole injection layer or a hole transport layer, wherein the hole injection layer or the hole transport layer includes a compound including an arylamino group, a carbazole group, or a benzocarbazole group.
The organic light-emitting device of the present specification may be manufactured using materials and methods well known in the art, except that one or more of the organic layers contains the heterocyclic compound of the present specification, that is, the heterocyclic compound represented by chemical formula 1.
When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device of the present specification may be manufactured by sequentially 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 (PVD: physical Vapor Deposition) such as sputtering or electron 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 this method, the second electrode material, the organic layer, and the first electrode material may be sequentially deposited on the substrate to manufacture an organic light-emitting device. In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum evaporation method but also in a solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (international patent application publication No. 2003/012890). However, the manufacturing method is not limited thereto.
According to an embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
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 specification 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: al or SnO 2 : a combination of a metal such as Sb and an oxide; poly (3-methylthiophene),Poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but 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, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole-transporting substance is preferably a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, and has a large mobility to the holes. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
The electron blocking layer is a layer that prevents holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer, and thus can improve the lifetime and efficiency of the device, and can be formed at an appropriate portion between the light emitting layer and the electron injection layer using a known material.
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 ) Carbazole-based compound, dimeric styryl (dimeric styryl) compound, BAlq, 10-hydroxybenzoquinoline-metal compound, benzoThe azole, benzothiazole, and benzimidazole compounds, poly (p-phenylene vinylene) (PPV) polymers, spiro (spiro) compounds, polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and trapezoidal furan Compounds, pyrimidine 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 a substituted or unsubstituted aromatic condensed ring derivative having an arylamino group, and includes pyrene, anthracene having an arylamino group,Bisindenopyrene and the like, in which a styrylamine compound is substituted on a substituted or unsubstituted arylamineAt least one arylvinyl compound substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl and arylamino. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The electron transporting substance of the electron transporting layer is a layer capable of receiving electrons from the electron injecting layer and transporting the electrons to the light emitting layer. The electron transporting material is preferably a material that can well inject electrons from the cathode and transfer the electrons to the light-emitting layer, and has a high mobility for electrons. 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 with any desired cathode material as used in the 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. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: 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 five-membered ring derivatives, and the like thereof, but are not limited theretoHere.
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 (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed generally under the same conditions as those of the hole injection layer. Specifically, there areThe diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
According to an embodiment of the present specification, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
Modes for carrying out the invention
< representative production example >
The compound according to an embodiment of the present specification can be produced by a production method described below.
For example, the compounds of the above chemical formulas 1-1 and 1-2 may be bonded to a substituent by a method (Suzuki reaction, boriding reaction, buchwald reaction, etc.) known in the art, and the kind, position or number of the substituent may be changed according to a technique known in the art.
The method for producing the compound of chemical formula 1 and the production of an organic light-emitting device using the same are specifically described in the following production examples. However, the following production examples are illustrative of the present invention, and the scope of the present invention is not limited thereto.
< production example >
Preparation of Compound 1
10g (21.74 mmol) of core A, 7.2g (28.26 mmol) of bis (pinacolato) diboron, 4.3g (43.48 mmol) of potassium acetate and 4mol% of [1,1' -bis (diphenylphosphino) ferrocene]Palladium dichloride ([ 1,1' -Bis (diphenylphosphino) ferrocene)]dichloropalladium (II)) to 60ml of twoThe mixture was stirred at 100℃for 12 hours in an alkane. After the completion of the reaction, the mixture was cooled to room temperature, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was then added thereto, stirred, filtered through a silica gel pad (silica pad), and concentrated under reduced pressure. Purifying by column chromatographyThus, 8.3g (75% yield) of intermediate 1-1 was obtained.
8.3g (16.33 mmol) of intermediate 1-1, 4.4g (16.33 mmol) of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3mol% of tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphine) paladium) were added to 50ml of tetrahydrofuran, and a solution obtained by dissolving 48.99mmol of potassium carbonate in 25ml of water was mixed thereto. After stirring at 80℃for 12 hours, the reaction was terminated, cooled to room temperature, and water and an organic layer were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydr ous magnesium sulfate) was added and stirred. After filtration through a Silica gel pad (Silica pad), the solution was concentrated under reduced pressure and purified by column chromatography to obtain 6.8g (68% yield) of intermediate 1-2.
6.8g (11.09 mmol) of intermediate 1-2 and 1.9g (11.09 mmol) of 9H-carbazole and 1.3g (13.31 mmol) of sodium tert-butoxide were added to 50ml of toluene, and the mixture was heated while stirring.
2mol% of bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone) paladium (0)) and 4mol% of 4, 5-bis (diphenylphosphine) -9, 9-dimethylxanthene (xanthos) were added at 100℃and the reaction was terminated after stirring for 10 hours, cooled to room temperature, and water and an organic layer were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added and stirred. After filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure and purified by column chromatography, whereby 5.9g (72% yield) of compound 1 was obtained.
MS:[M+H]+＝745
Preparation of Compound 2
Intermediate 2-1 was obtained in a yield of 81% by performing the reaction and purification in the same manner as in the synthesis of the above-mentioned intermediate 1-2 except that 10g (19.68 mmol) of intermediate 1-1 and 6.1g (19.68 mmol) of 2-bromo-4, 6-diphenylpyridine were used.
8.0g (68% yield) of compound 2 was obtained by performing the reaction and purification in the same manner as in the synthesis of the above-mentioned compound 1 except that 9.7g (15.87 mmol) of intermediate 2-1 and 2.7g (15.87 mmol) of 9H-carbazole were used.
MS:[M+H]+＝743
Preparation of Compound 3
Intermediate 3-1 was obtained in 79% yield by performing the reaction and purification in the same manner as in the synthesis of the above-mentioned intermediate 1-2 except that 10g (19.68 mmol) of intermediate 1-1 and 3.6g (19.68 mmol) of 3-bromophenyl nitrile were used.
6.3g (66% yield) of Compound 3 was obtained by performing the reaction and purification in the same manner as in the synthesis of Compound 1 above except that 7.5g (15.53 mmol) of intermediate 3-1 and 2.6g (15.53 mmol) of 9H-carbazole were used.
MS:[M+H]+＝615
Preparation of Compound 4
Intermediate 4-1 was obtained in 80% yield by performing the reaction and purification in the same manner as in the synthesis of the above-mentioned intermediate 1-2 except that 10g (19.68 mmol) of intermediate 1-1 and 4.8g (19.68 mmol) of 4-bromodibenzo [ b, d ] furan were used.
Reaction and purification were carried out in the same manner as in the synthesis of the above-mentioned compound 1 except that 8.6g (15.69 mmol) of intermediate 4-1 and 2.6g (15.69 mmol) of 9H-carbazole were used, whereby 7.6g (71% yield) of compound 4 was obtained.
MS:[M+H]+＝680
Preparation of Compound 5
10g (16.31 mmol) of intermediate 1-2, 5.4g (21.20 mmol) of bis (pinacolato) diboron, 3.2g (32.62 mmol) of potassium acetate, 4mol% of bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone) paladium) and 8mol% of tricyclohexylphosphine are added to 50ml of dicyclohexylphosphine The mixture was stirred at 100℃for 12 hours in an alkane. Cooling to room temperature after the reaction, adding anhydrous magnesium sulfate (anhydrous magnesium sulfate), stirringMixing, filtering with silica gel pad (silica pad), and concentrating under reduced pressure. Column chromatography purification was performed to obtain intermediate 5-1 in a yield of 64%.
7.4g (10.49 mmol) of intermediate 5-1 and 3.4g (10.49 mmol) of 2-bromo-9-phenyl-9H-carbazole and 3mol% of tetrakis (triphenylphosphine) palladium (Tetrakis (triphenyl phosphine) paladium) were added to 50ml of tetrahydrofuran, and a solution obtained by dissolving 31.47mmol of potassium carbonate in 25ml of water was mixed thereto. After stirring at 80℃for 12 hours, the reaction was terminated, cooled to room temperature, and water and an organic layer were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydr ous magnesium sulfate) was added and stirred. After filtration through a Silica pad (Silica pad), the solution was concentrated under reduced pressure and purified by column chromatography to obtain 6.6g (77% yield) of compound 5.
MS:[M+H]+＝821
Preparation of Compound 6
6.2g (72% yield) of Compound 6 was obtained by performing the reaction and purification in the same manner as in the synthesis of Compound 5 above except that 7.4g (10.49 mmol) of intermediate 5-1 and 3.4g (10.49 mmol) of 3-bromo-9-phenyl-9H-carbazole were used.
MS:[M+H]+＝821
Preparation of Compound 7
Reaction and purification were carried out in the same manner as in the synthesis of the above-mentioned compound 5 except that 7.4g (10.49 mmol) of the intermediate 5-1 and 3.5g (10.49 mmol) of triphenylbromosilane were used, whereby 5.8g (66% yield) of the compound 7 was obtained.
MS:[M+H]+＝838
Preparation of Compound 8
7.0g (73% yield) of compound 8 was obtained by performing the reaction and purification in the same manner as in the synthesis of the above-described compound 5 except that 7.4g (10.49 mmol) of intermediate 5-1 and 4.3g (10.49 mmol) of (4-bromophenyl) triphenylsilane were used.
MS:[M+H]+＝914
Preparation of Compound 9
10g (21.74 mmol) of core B (core B), 7.2g (28.26 mmol) of bis (pinacolato) diboron, 4.3g (43.48 mmol) of potassium acetate and 4mol% of [1,1' -bis (diphenylphosphino) ferrocene]Palladium dichloride ([ 1,1' -Bis (diphenylphosphino) ferrocene)]dichloropalladium (II)) to 60ml of twoThe mixture was stirred at 100℃for 12 hours in an alkane. After the completion of the reaction, the mixture was cooled to room temperature, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was then added thereto, stirred, filtered through a silica gel pad (silica pad), and concentrated under reduced pressure. Column chromatography purification was performed, whereby 7.8g (71% yield) of intermediate 9-1 was obtained.
7.8g (15.35 mmol) of intermediate 9-1, 4.1g (15.35 mmol) of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3mol% of tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphine) paladium) were added to 50ml of tetrahydrofuran, and a solution obtained by dissolving 46.05mmol of potassium carbonate in 25ml of water was mixed thereto. After stirring at 80℃for 12 hours, the reaction was terminated, cooled to room temperature, and water and an organic layer were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydr ous magnesium sulfate) was added and stirred. After filtration through a Silica gel pad (Silica pad), the solution was concentrated under reduced pressure and purified by column chromatography to obtain 6.0g (64% yield) of intermediate 9-2.
6.0g (9.79 mmol) of intermediate 9-2, 1.6g (9.79 mmol) of 9H-carbazole, and 1.1g (11.75 mmol) of sodium tert-butoxide were added to 50ml of toluene, and the mixture was heated while stirring.
2mol% of bis (dibenzylideneacetone) palladium (0) (Bis (dibenzylideneacetone) paladium (0)) and 4mol% of 4, 5-bis (diphenylphosphine) -9, 9-dimethylxanthene (xantphos) were added at 100℃and after stirring for 10 hours, the reaction was terminated, cooled to room temperature, and water and an organic layer were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added and stirred. After filtration through a silica gel pad (S iica pad), the solution was concentrated under reduced pressure and purified by column chromatography to obtain 5.1g (70% yield) of compound 9.
MS:[M+H]+＝745
Preparation of Compound 10
Intermediate 10-1 was obtained in 77% yield by performing the reaction and purification in the same manner as in the synthesis of intermediate 9-2 above except that 10g (19.68 mmol) of intermediate 9-1 and 6.1g (19.68 mmol) of 2-bromo-4, 6-diphenylpyridine were used.
7.3g (65% yield) of compound 10 was obtained by performing the reaction and purification in the same manner as in the synthesis of the above-mentioned compound 9 except that 9.3g (15.22 mmol) of intermediate 10-1 and 2.5g (15.22 mmol) of 9H-carbazole were used.
MS:[M+H]+＝743
Preparation of Compound 11
Intermediate 11-1 was obtained in 73% yield by performing the reaction and purification in the same manner as in the synthesis of the above-mentioned intermediate 9-2 except that 10g (19.68 mmol) of intermediate 9-1 and 3.6g (19.68 mmol) of 3-bromophenyl nitrile were used.
Reaction and purification were carried out in the same manner as in the synthesis of the above-mentioned compound 9 except that 6.9g (14.28 mmol) of intermediate 11-1 and 2.4g (14.28 mmol) of 9H-carbazole were used, whereby 5.9g (68% yield) of compound 11 was obtained.
MS:[M+H]+＝615
Preparation of Compound 12
Intermediate 12-1 was obtained in 77% yield by performing the reaction and purification in the same manner as in the synthesis of the above intermediate 9-2 except that 10g (19.68 mmol) of intermediate 9-1 and 4.8g (19.68 mmol) of 4-bromodibenzo [ b, d ] furan were used.
Reaction and purification were carried out in the same manner as in the synthesis of the above-mentioned compound 9 except that 8.3g (15.23 mmol) of the intermediate 12-1 and 2.5g (15.23 mmol) of 9H-carbazole were used, whereby 7.0g (68% yield) of the compound 12 was obtained.
MS:[M+H]+＝680
Preparation of Compound 13
10g (16.31 mmol) of intermediate 9-2, 5.4g (21.20 mmol) of bis (pinacolato) diboron, 3.2g (32.62 mmol) of potassium acetate, 4mol% of bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone) paladium), and 8mol% of tricyclohexylphosphine are added to 50ml of dicyclohexylphosphineThe mixture was stirred at 100℃for 12 hours in an alkane. After the completion of the reaction, the mixture was cooled to room temperature, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was then added thereto, stirred, and filtered through a silica gel pad (s ilica pad), followed by concentration under reduced pressure. Column chromatography purification was performed to obtain intermediate 13-1 in 69% yield.
7.9g (11.20 mmol) of intermediate 13-1, 3.6g (11.20 mmol) of 2-bromo-9-phenyl-9H-carbazole, and 3mol% of tetrakis (triphenylphosphine) palladium (Tetrakis (triphenylphosphine) paladium) were added to 50ml of tetrahydrofuran, and a solution obtained by dissolving 33.60mmol of potassium carbonate in 25ml of water was mixed thereto. After stirring at 80℃for 12 hours, the reaction was terminated, cooled to room temperature, and water and an organic layer were separated. Only the organic layer was collected, anhydrous magnesium sulfate (anhydr ous magnesium sulfate) was added and stirred. After filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure and purified by column chromatography to obtain 6.9g (75% yield) of compound 13.
MS:[M+H]+＝821
Preparation of Compound 14
6.3g (73% yield) of Compound 14 was obtained by performing the reaction and purification in the same manner as in the synthesis of Compound 13 above except that 7.4g (10.49 mmol) of intermediate 13-1 and 3.4g (10.49 mmol) of 3-bromo-9-phenyl-9H-carbazole were used.
MS:[M+H]+＝821
Preparation of Compound 15
Reaction and purification were carried out in the same manner as in the synthesis of the above-mentioned compound 13 except that 7.4g (10.49 mmol) of the intermediate 13-1 and 3.5g (10.49 mmol) of triphenylbromosilane were used, whereby 6.2g (71% yield) of the compound 15 was obtained.
MS:[M+H]+＝838
Preparation of Compound 16
6.8g (71% yield) of Compound 16 was obtained by performing the reaction and purification in the same manner as in the synthesis of Compound 13 above, except that 7.4g (10.49 mmol) of intermediate 13-1 and 4.3g (10.49 mmol) of (4-bromophenyl) triphenylsilane were used.
MS:[M+H]+＝914
Examples (example)
Experimental example 1-1 ]
ITO (Indium tin oxide) toThe glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then 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, the composition according to m-MTDATA (60 nm)/TCTA (80 nm)/bulk +10% Ir (ppy) 3 (300nm)/BCP(10nm)/Alq 3 The order of (30 nm)/LiF (1 nm)/Al (200 nm) constituted a light-emitting device, and as the above-described host, compound 1 was used, thereby manufacturing an organic EL device.
m-MTDATA、TCTA、Ir(ppy) 3 And the structure of BCP are shown below, respectively.
Experimental examples 1-2 ]
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 2 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 3
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 3 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 4
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 4 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 5
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 5 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 6
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 6 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 7
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 7 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 8
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 8 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 9
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 9 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 10
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 10 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 11
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 11 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 12
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 12 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 13
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 13 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 14
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 14 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 15
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 15 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 16
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 16 was used instead of compound 1 in example 1-1.
Comparative examples 1 to 1 ]
An organic light-emitting device was produced in the same manner as in example 1-1 except that GH 1 was used instead of Compound 1 in example 1-1.
Comparative examples 1 to 2
An organic light-emitting device was produced in the same manner as in example 1-1 except that GH 2 was used instead of Compound 1 in example 1-1.
Comparative examples 1 to 3
An organic light-emitting device was produced in the same manner as in example 1-1 except that GH 3 was used instead of Compound 1 in example 1-1.
The results of table 1 were obtained when current was applied to the organic light emitting devices fabricated by experimental examples 1-1 to 1-16, comparative examples 1-1 and 1-3.
TABLE 1
As a result of the experiment, the green organic EL devices of experimental examples 1-1 to 1-16 using the compounds represented by the compounds 1 to 16 related to the present invention as host substances of the light emitting layers showed excellent performance in terms of current efficiency and driving voltage, compared to the green organic EL devices of comparative examples 1-1 to 1-3 using the existing GH.
Experimental example 2-1 ]
An organic light-emitting diode was produced in which compound 1 was used as a host for a light-emitting substance layer. First, a glass substrate having an ITO (including a reflecting plate) electrode attached thereto was washed with isopropyl alcohol, acetone, and deionized Water (DI Water) for 5 minutes at 40mm by 0.5mm in thickness by ultrasonic wave, and then dried in an Oven (Oven) at 100 ℃. After the substrate is washed, O is performed in a vacuum state 2 The plasma treatment was carried out for 2 minutes, and the resulting film was transferred to a vapor deposition chamber for vapor deposition of another layer on the upper part. At about 10 -7 Organic layers were evaporated from the heated boat by evaporation in the following order under a vacuum. At this time, the vapor deposition rate of the organic material was set to be
A hole injection layer (HIL: HAT-CN,) A hole transport layer (HTL: NPB (NPB)/(NPB)>) Electron blocking layer (EBL: mCBP (micro-encapsulated fiber reinforced plastics)>) Light-emitting substance layer (EML: using compound 1 as a host, 4CzIPN was doped as a fluorescent substance by 30 wt%, +. >) Hole blocking layer (HBL: b3PYMPM,>) An electron transport layer (ETL: TPBi, & gt>) Electron injection layer (EIL: liF (LiF)>) And a cathode (Al: />)。
CPL (coating layer) is formed and then encapsulated with glass. After vapor deposition of these layers, the film was transferred from the vapor deposition chamber into a drying oven, and then encapsulated with a UV curable epoxy resin and a water absorbing agent (getter).
Experimental example 2-2 ]
An organic light-emitting device was fabricated in the same manner as in example 2-1, except that compound 2 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 3
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 3 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 4
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 4 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 5
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 5 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 6
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 6 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 7
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 7 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 8
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 8 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 9
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 9 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 10
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 10 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 11
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 11 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 12
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 12 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 13
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 13 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 14
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 14 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 15
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 15 was used instead of compound 1 in example 2-1.
Experimental examples 2 to 16
An organic light-emitting device was produced in the same manner as in example 2-1 except that compound 16 was used instead of compound 1 in example 2-1.
Comparative example 2-1 ]
An organic light-emitting device was produced in the same manner as in example 2-1 except that GH 1 was used instead of Compound 1 in example 2-1.
Comparative examples 2 to 2 ]
An organic light-emitting device was produced in the same manner as in example 2-1 except that GH 2 was used instead of Compound 1 in example 2-1.
Comparative examples 2 to 3
An organic light-emitting device was produced in the same manner as in example 2-1 except that GH 3 was used instead of Compound 1 in example 2-1.
When current was applied to the organic light emitting devices fabricated by experimental examples 2-1 to 2-16 and comparative examples 2-1 and 2-3, the following results of table 2 were obtained.
TABLE 2
In the case where the organic compound synthesized according to the present invention is used as a host of the light-emitting substance layer, the driving voltage is reduced and the External Quantum Efficiency (EQE) is improved as compared with the case where the compounds of comparative examples 2-1 to 2-3 are used as a host of the light-emitting substance layer. Finally, it was confirmed that by applying the organic compound of the present invention to an organic light-emitting layer, the driving voltage of a light-emitting diode can be reduced, the light-emitting efficiency can be improved, and the color purity can be improved. Therefore, the organic light-emitting diode using the organic compound of the present invention can be applied to a light-emitting device such as an organic light-emitting diode display device and/or a lighting device, etc., which has reduced power consumption and improved light-emitting efficiency and device lifetime.

Claims (9)

1. A heterocyclic compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
any one of G1 and G2 is-L2-Ar 2, the balance is hydrogen,
l1 and L2 are identical to or different from each other and are each independently a direct bond or a phenylene group,
ar1 is an electron donating group EDG, ar2 is an electron withdrawing group EWG; or Ar1 is an electron withdrawing group EWG, ar2 is an electron donating group EDG,
wherein the electron donating group EDG is selected from the group represented by the following formulas A-2, A-3, and A-8:
Formula A-2
Chemical formula A-3
Formula A-8
In the chemical formulas A-2, A-3 and A-8,
the Q2, Q3, Q12, Q13, Q14 and Q101 are the same as or different from each other, each independently is hydrogen or phenyl,
q2 is a number of times 1,
q3 is a number of times 1,
q12 to q14 are each 1,
wherein the electron withdrawing group EWG is selected from groups represented by the following formulas B-1 to B-4:
chemical formula B-1
Chemical formula B-2
Chemical formula B-3
Chemical formula B-4
In the chemical formulas B-1 to B-4,
at least one of X1 to X3 is N, the rest is CH,
x4 is CT4, X5 is CT5, X6 is CT6, X7 is CT7,
y1 is O or S, and the total number of the components is equal to or less than zero,
t1 and T2 are identical to or different from each other and are each independently hydrogen or phenyl,
t3 to T7 are hydrogen and,
q is 1, and the number of the groups is 1,
the t3 is a number of times 1,
refers to a portion bonded to the chemical formula 1,
r1 and R2 are hydrogen,
m and n are each 1.
2. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1 or 1-2:
chemical formula 1-1
Chemical formula 1-2
In the chemical formulas 1-1 and 1-2,
l1, L2, ar1, ar2, R1, R2, m and n are as defined in the chemical formula 1.
3. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is selected from the following compounds:
/>
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/>
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4. An organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains the heterocyclic compound according to any one of claims 1 to 3.
5. The organic light-emitting device according to claim 4, wherein the organic layer comprises a light-emitting layer comprising the heterocyclic compound.
6. The organic light-emitting device according to claim 4, wherein the organic layer comprises a light-emitting layer comprising the heterocyclic compound as a host of the light-emitting layer.
7. The organic light-emitting device according to claim 4, 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.
8. The organic light-emitting device according to claim 4, wherein the organic layer comprises a hole blocking layer comprising the heterocyclic compound.
9. The organic light-emitting device of claim 4, wherein the organic layer comprises an electron modulating layer comprising the heterocyclic compound.
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