CN109912523B - 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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CN109912523B
CN109912523B CN201910006879.3A CN201910006879A CN109912523B CN 109912523 B CN109912523 B CN 109912523B CN 201910006879 A CN201910006879 A CN 201910006879A CN 109912523 B CN109912523 B CN 109912523B
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张焚在
李东勋
许东旭
韩美连
姜敏英
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Abstract

The invention provides a heterocyclic compound and an organic light-emitting device comprising the same. The present invention provides a compound represented by formula 1. [ 1 ]]
Figure DDA0001935808100000011
。

Description

Heterocyclic compound and organic light-emitting device comprising same
The present application is a divisional application of chinese patent application having application date 2015, month 4 and 2, application number "201580017744.7" and the title of the present application "heterocyclic compound and organic light-emitting device comprising the same".
Technical Field
The present invention claims priority and rights of korean patent application No. 10-2014-0040818, which was filed on 4 th month 2014 to the korean intellectual property office, korean patent application No. 10-2015-0017929, which was filed on 5 th month 2015 to the korean intellectual property office, and korean patent application No. 10-2015-0045586, which was filed on 31 th month 2015 to the korean intellectual property office, the entire contents of which are incorporated herein by reference.
The present invention relates to a heterocyclic compound and an organic light-emitting device 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 material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Herein, the organic material layer may have a multi-layered structure composed of different materials to improve efficiency and stability of the organic light emitting device in many cases, and for example, may be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected from an anode into the organic material layer and electrons are injected from a cathode into the organic material layer, and when the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons drop to a ground state again.
There is a continuous need to develop new materials for the above-mentioned organic light emitting devices.
Disclosure of Invention
Technical problem
The present specification describes heterocyclic compounds and organic light-emitting devices comprising the same.
Technical solution
Exemplary embodiments of the present invention provide compounds represented by the following formula 1:
[ 1]
Figure BDA0001935808080000021
In the formula (1) of the present invention,
ar1 and Ar2 are identical to each other and are phenyl, which is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfinyl groups, arylsulfinyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, arylphosphine groups, and heterocyclic groups; biphenyl, unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfinyl groups, arylsulfinyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, arylphosphine groups, and heterocyclic groups; naphthyl, which is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfinyl groups, arylsulfinyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, arylphosphine groups, and heterocyclic groups; or phenanthryl, which is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfinyl group, arylsulfinyl group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamino group, aralkylamino group, heteroarylamino group, arylamino group, arylphosphine group and heterocyclic group,
L is a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene,
r1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; a substituted or unsubstituted alkylsulfinyl group; a substituted or unsubstituted aryl sulfinyl group; a substituted or unsubstituted alkenyl group; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; a substituted or unsubstituted alkylamino group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroaryl amine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamino group; substituted or unsubstituted aryl phosphino; substituted or unsubstituted phosphine oxide groups; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
R3 and R4 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; a substituted or unsubstituted alkylsulfinyl group; a substituted or unsubstituted aryl sulfinyl group; a substituted or unsubstituted alkenyl group; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; a substituted or unsubstituted alkylamino group; a substituted or unsubstituted aralkylamine group; substituted or unsubstituted aryl phosphino; or a substituted or unsubstituted phosphine oxide group; or may combine with adjacent groups to form a substituted or unsubstituted ring,
m is an integer of 1 to 5,
a is an integer of 0 to 3, and
b is an integer of 0 to 4, and
When m, a and b are 2 or more, respectively, the structures in brackets are the same or different from each other.
Moreover, one exemplary embodiment of the present invention provides: an organic light emitting device comprising: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound of formula 1.
Advantageous effects
The compounds described in the present specification can be used as materials for organic material layers of organic light emitting devices. The compound according to at least one exemplary embodiment may increase efficiency and improve low driving voltage and/or lifetime characteristics in an organic light emitting device. In particular, the compounds described in this specification can be used as materials for hole injection, hole transport, hole injection and hole transport, luminescence, electron transport or electron injection. Further, the compound described in the present specification can be preferably used as a material for a light-emitting layer, electron transport, or electron injection, and more preferably used as a material for electron transport or electron injection.
Drawings
Fig. 1 illustrates an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.
Fig. 3 illustrates MS data results for compound 67 prepared in the example.
Detailed Description
The present invention will be described in more detail hereinafter.
An exemplary embodiment of the present invention provides a compound represented by formula 1.
Examples of substituents will be described below, but are not limited thereto.
In the present specification, the term "substituted or unsubstituted" means that the group is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio; arylthio; an alkylsulfinyl group; aryl sulfinyl; a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; and a heterocyclic group, or a substituent to which two or more substituents of the substituents exemplified above are attached is substituted or unsubstituted. For example, a "substituent to which two or more substituents are attached" may be a biphenyl group. That is, the biphenyl group may also be an aryl group, and may be understood as being two phenyl-linked substituents.
According to an exemplary embodiment of the present invention, the term "substituted or unsubstituted" may preferably mean that the group is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; an alkyl group; an alkoxy group; and aryl.
According to an exemplary embodiment of the present invention, the compound represented by formula 1 may be unsubstituted or substituted with at least one deuterium.
In this specification, an "adjacent" group may refer to a substituent substituted for an atom directly attached to an atom substituted with a corresponding substituent, a substituent disposed spatially closest to a corresponding substituent, or another substituent substituted for an atom substituted with a corresponding substituent. For example, two substituents substituted at ortho positions of the benzene ring, as well as two substituents substituted for the same carbon in the aliphatic ring, may be understood as groups "adjacent" to each other.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. In particular, the carbonyl group may be a compound having the following structure, but is not limited thereto.
Figure BDA0001935808080000051
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 25 carbon atoms. In particular, the ester group may be a compound having the following structure, but is not limited thereto.
Figure BDA0001935808080000052
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. In particular, the imide group may be a compound having the following structure, but is not limited thereto.
Figure BDA0001935808080000061
In this specification, the silyl group may be represented by the formula-SiRR 'R ", and R, R' and R" may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like, but are not limited thereto.
In this specification, the boron group may be represented by the formula-BRR 'R ", and R, R' and R" may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the boron group include trimethylboron group, triethylboron group, t-butyldimethylboro group, triphenylboron group, phenylboron group, and the like, but are not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to yet another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-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, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has a number of carbon atoms of 2 to 20. According to another exemplary embodiment, the alkenyl group has a number of carbon atoms of 2 to 10. According to yet another exemplary embodiment, the alkenyl group has a number of carbon atoms of 2 to 6. Specific examples of the alkenyl group include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthalen-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl,
Figure BDA0001935808080000071
Radical, styryl, etc., but is not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another exemplary embodiment, the cycloalkyl group has a number of carbon atoms ranging from 3 to 20. According to yet another exemplary embodiment, the cycloalkyl group has a number of carbon atoms of 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.
In the present specification, specific examples of the arylamine group include 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 comprising the two or more aryl groups may comprise a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group.
Specific examples of the arylamine group include, but are not limited to, phenylamine, naphthylamine, biphenylamine, anthrylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthrylamine, diphenylamine group, phenylnaphthylamine group, xylylamine group, phenyltolylamino group, carbazole, triphenylamine group, and the like.
In the present specification, examples of the heteroarylamino group include a substituted or unsubstituted mono-heteroarylamino group, a substituted or unsubstituted di-heteroarylamino group, or a substituted or unsubstituted tri-heteroarylamino group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroaryl amine group comprising two or more heterocyclic groups may comprise a monocyclic heterocyclic group, a polycyclic heterocyclic group, or both a monocyclic heterocyclic group and a polycyclic heterocyclic group.
In the present specification, the arylheteroarylamine group means an amine group substituted with an aryl group and a heterocyclic group.
In the present specification, examples of the arylphosphino group include a substituted or unsubstituted monoarylphosphino group, a substituted or unsubstituted diarylphosphino group, or a substituted or unsubstituted triarylphosphino group. The aryl group in the aryl phosphino group may be a monocyclic aryl group or a polycyclic aryl group. The aryl phosphine group comprising two or more aryl groups may comprise a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group.
In the present specification, examples of the arylamine group refer to a substituted or unsubstituted monocyclic diarylamino group, a substituted or unsubstituted polycyclic diarylamino group, or a substituted or unsubstituted monocyclic and polycyclic diarylamino group.
In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has a number of carbon atoms of 6 to 30. According to an exemplary embodiment, the aryl group has a number of carbon atoms of 6 to 20. When the aryl group is a monocyclic aryl group, examples of the monocyclic aryl group include phenyl, biphenyl, terphenyl, and the like, but are not limited thereto. Examples of the polycyclic aryl groups include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl,
Figure BDA0001935808080000083
A group, a fluorenyl group, a biphenylyl group, and the like, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure.
When the fluorenyl group is substituted, the fluorenyl group may be
Figure BDA0001935808080000081
Figure BDA0001935808080000082
Etc. However, the fluorenyl group is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing one or more of N, O, P, S, si and Se as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoxazolyl, oxadiazolyl (oxadiazolyl group), thiadiazolyl (thiadiazolyl group), benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In this specification, the description of the heterocyclic groups described above applies to heteroaryl groups, except that heteroaryl groups are aromatic groups.
In the present specification, the description of the above aryl group can be applied to aryl groups of aryloxy group, arylthio group, arylsulfinyl group, arylphosphino group, aralkyl group, aralkylamino group, aralkenyl group, alkylaryl group, arylamino group and arylheteroarylamino group.
In the present specification, the description of the above alkyl group is applicable to an alkyl group of an alkylthio group, an alkylsulfinyl group, an aralkyl group, an aralkylamino group, an alkylaryl group, and an alkylamino group.
In the present specification, the description of the above heterocyclic group may be applied to heteroaryl groups of heteroaryl groups, heteroarylamine groups and arylheteroarylamine groups.
In the present specification, the description of the above alkenyl group is applicable to an alkenyl group of an aralkenyl group.
In the present specification, the above description of aryl groups can be applied to arylene groups, except that arylene groups are divalent groups.
In the present specification, the description of the above heterocyclic group is applicable to the heteroarylene group, except that the heteroarylene group is a divalent group.
In the present specification, the meaning of a ring formed by bonding to an adjacent group means that a substituted or unsubstituted aliphatic hydrocarbon ring is formed by bonding to an adjacent group; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; and condensed rings thereof.
In the present specification, the aliphatic hydrocarbon ring refers to a ring composed of only carbon atoms and hydrogen atoms, which is a ring that is not an aromatic group.
In the present specification, examples of the aromatic hydrocarbon ring include phenyl, naphthyl, anthracenyl, and the like, but are not limited thereto.
In the present specification, the aliphatic heterocyclic ring refers to an aliphatic ring containing one or more hetero atoms.
In this specification, the aromatic heterocycle means an aromatic ring containing one or more hetero atoms.
In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring, and the aromatic heterocyclic ring may be monocyclic or polycyclic.
According to an exemplary embodiment of the present invention, formula 1 may be represented by any one of the following formulas 2 to 4.
[ 2]
Figure BDA0001935808080000101
[ 3]
Figure BDA0001935808080000102
[ 4]
Figure BDA0001935808080000103
In the formulae 2 to 4,
ar1, ar2, L, R3, R4, a, b and m are as defined in formula 1,
r11, R12, R21 and R22 are as defined for R3 and R4,
x1 and X2 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; a substituted or unsubstituted alkylsulfinyl group; a substituted or unsubstituted aryl sulfinyl group; a substituted or unsubstituted alkenyl group; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; a substituted or unsubstituted alkylamino group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroaryl amine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamino group; substituted or unsubstituted aryl phosphino; or a substituted or unsubstituted phosphine oxide group; or may combine with adjacent groups to form a substituted or unsubstituted ring,
r11 and r12 are the same or different from each other and are each independently an integer of 0 to 5,
r21 and r22 are the same or different from each other and each independently is an integer of 0 to 4, and
when r11, r12, r21 and r22 are 2 or more, respectively, the structures in brackets are the same or different from each other.
According to an exemplary embodiment of the present invention, formula 1 may be represented by any one of the following formulas 5 to 8.
[ 5]
Figure BDA0001935808080000111
[ 6]
Figure BDA0001935808080000121
[ 7]
Figure BDA0001935808080000122
[ 8]
Figure BDA0001935808080000123
In the formulae 5 to 8,
ar1, ar2, L, R1 to R4, m, a and b are as defined in formula 1.
According to an exemplary embodiment of the present invention, formula 2 may be represented by any one of the following formulas 2-1 to 2-4.
[ 2-1]
Figure BDA0001935808080000131
[ 2-2]
Figure BDA0001935808080000132
[ 2-3]
Figure BDA0001935808080000141
[ 2-4]
Figure BDA0001935808080000142
In the formulas 2-1 to 2-4,
ar1, ar2, L, R3, R4, a and b are as defined in formula 1,
the definitions of R11, R12, R11 and R12 are the same as those defined in formula 2.
According to an exemplary embodiment of the present invention, formula 3 may be represented by any one of the following formulas 3-1 to 3-4.
[ 3-1]
Figure BDA0001935808080000151
[ 3-2]
Figure BDA0001935808080000152
[ 3-3]
Figure BDA0001935808080000161
[ 3-4]
Figure BDA0001935808080000162
In the formulae 3-1 to 3-4,
ar1, ar2, L, R3, R4, a and b are as defined in formula 1, and
the definitions of R21, R22, R21 and R22 are the same as those defined in formula 3.
According to an exemplary embodiment of the invention, X1 and X2 are identical to or different from each other and are each independently a substituted or unsubstituted alkyl group.
According to an exemplary embodiment of the present invention, X1 and X2 are the same or different from each other and are each independently an alkyl group.
According to an exemplary embodiment of the invention, X1 and X2 are methyl.
According to an exemplary embodiment of the invention, ar1 and Ar2 are identical to each other and are phenyl, unsubstituted or substituted with one or more substituents selected from deuterium and alkyl; biphenyl, unsubstituted or substituted with one or more substituents selected from deuterium, alkyl and aryl; naphthyl, unsubstituted or substituted with one or more substituents selected from deuterium, alkyl and aryl; or phenanthryl, unsubstituted or substituted with one or more substituents selected from deuterium, alkyl and aryl.
According to an exemplary embodiment of the invention, ar1 and Ar2 are identical to each other and are phenyl, unsubstituted or deuterium substituted; biphenyl, unsubstituted or deuterium-substituted; naphthyl, unsubstituted or substituted with deuterium; or phenanthryl, unsubstituted or substituted with deuterium.
According to an exemplary embodiment of the invention, ar1 and Ar2 are identical to each other and are phenyl, biphenyl, naphthyl or phenanthryl.
According to an exemplary embodiment of the present invention, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a silyl group; a boron base; an alkyl group; cycloalkyl; an alkoxy group; an aryloxy group; alkylthio; arylthio; an alkylsulfinyl group; aryl sulfinyl; alkenyl groups; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl heteroaryl amino; aryl phosphino; a phosphine oxide group; aryl, unsubstituted or substituted with deuterium, alkyl or alkoxy; or a heterocyclic group, or may be combined with an adjacent group to form a ring.
According to an exemplary embodiment of the present invention, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or substituted or unsubstituted aryl, or are combined with each other to form a substituted or unsubstituted ring.
According to an exemplary embodiment of the present invention, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; alkyl, unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfinyl groups, arylsulfinyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, arylphosphine groups, and heterocyclic groups; or aryl, unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfinyl groups, arylsulfinyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, aryl phosphine groups and heterocyclic groups, or are combined with each other to form a ring, which is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfinyl groups, arylsulfinyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, arylphosphine groups, and heterocyclic groups.
According to an exemplary embodiment of the present invention, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; alkyl, unsubstituted or substituted with one or more substituents selected from deuterium, alkyl, alkoxy, and aryl; or aryl, unsubstituted or substituted with one or more substituents selected from deuterium, alkyl, alkoxy and aryl, or combined with each other to form a ring, said ring being unsubstituted or substituted with one or more substituents selected from deuterium, alkyl, alkoxy and aryl.
According to an exemplary embodiment of the present invention, R1 and R2 are the same or different from each other and are each independently hydrogen; an alkyl group; or aryl, unsubstituted or substituted with one or more substituents selected from deuterium, halogen groups, alkyl and alkoxy, or combined with each other to form a ring.
According to an exemplary embodiment of the invention, R1 and R2 are identical to or different from each other and are each independently a substituted or unsubstituted alkyl group; or substituted or unsubstituted monocyclic to tricyclic aryl groups, or are combined with each other to form a substituted or unsubstituted ring.
According to an exemplary embodiment of the invention, R1 and R2 are identical to or different from each other and are each independently a substituted or unsubstituted alkyl group; or substituted or unsubstituted phenyl, or are combined with each other to form a substituted or unsubstituted ring.
According to an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other and are each independently hydrogen, deuterium, a halogen group, an alkyl group, and an aryl group, or are combined with each other to form a ring.
According to an exemplary embodiment of the present invention, R1 and R2 are the same or different from each other and are each independently an alkyl group; and aryl, or are combined with each other to form a ring.
According to an exemplary embodiment of the present invention, R1 and R2 are the same or different from each other and are each independently an alkyl group; or phenyl groups, or are combined with each other to form a ring.
According to an exemplary embodiment of the present invention, R1 and R2 are the same or different from each other and are each independently methyl; or phenyl groups, or are combined with each other to form a ring.
According to an exemplary embodiment of the present invention, R3 and R4 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a silyl group; a boron base; an alkyl group; cycloalkyl; an alkoxy group; an aryloxy group; alkylthio; arylthio; an alkylsulfinyl group; aryl sulfinyl; alkenyl groups; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; aryl phosphino; or a phosphine oxide group.
According to an exemplary embodiment of the invention, R3 and R4 are identical to or different from each other and are each independently hydrogen, deuterium, a halogen group or an alkyl group.
According to an exemplary embodiment of the invention, R3 and R4 are hydrogen.
According to an exemplary embodiment of the invention, R4 is hydrogen.
According to an exemplary embodiment of the invention, R3 is hydrogen.
According to an exemplary embodiment of the invention, L is phenylene, unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfinyl groups, arylsulfinyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, arylphosphine groups, and heterocyclic groups; or biphenylene, unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfinyl groups, arylsulfinyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, arylphosphine groups, and heterocyclic groups.
According to an exemplary embodiment of the invention, L is phenylene; or biphenylene.
According to an exemplary embodiment of the present invention, L may be any one selected from the following structures.
Figure BDA0001935808080000191
/>
Figure BDA0001935808080000201
The structure may be unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio; arylthio; an alkylsulfinyl group; aryl sulfinyl; a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; and a heterocyclic group.
According to an exemplary embodiment of the invention, the
Figure BDA0001935808080000202
The moiety may be any one selected from the following structures. />
Figure BDA0001935808080000211
Figure BDA0001935808080000221
In the case of the construction described above, in which the first and second support members are arranged,
r1 and R2 are as defined in formula 1, and
the structure may be unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio; arylthio; an alkylsulfinyl group; aryl sulfinyl; a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; and a heterocyclic group.
According to an exemplary embodiment of the invention, m is 1.
According to an exemplary embodiment of the invention, m is 1 or 2.
According to an exemplary embodiment of the present invention, the compound of formula 1 may be any one selected from the following compounds:
Figure BDA0001935808080000231
/>
Figure BDA0001935808080000241
/>
Figure BDA0001935808080000251
/>
Figure BDA0001935808080000261
/>
Figure BDA0001935808080000271
/>
Figure BDA0001935808080000281
/>
Figure BDA0001935808080000291
/>
Figure BDA0001935808080000301
Figure BDA0001935808080000311
/>
the compound represented by formula 1 may be prepared based on the preparation examples to be described below. According to one exemplary embodiment, the compound may be prepared by a method such as the following reaction scheme 1.
[ reaction type 1]
Figure BDA0001935808080000312
In the case of the reaction scheme 1,
ar1, ar2, L, R1, R2, R3, R4, a, b and m are as defined in formula 1.
In particular, according to one exemplary embodiment of the present invention, the compound of formula 1 may be prepared by coupling a compound of a halogen-substituted triazine derivative with a boric acid or boric acid derivative-substituted aromatic compound using a palladium-catalyzed reaction.
Further, the present invention provides an organic light emitting device including the compound represented by any one of formulas 1 to 8.
An exemplary embodiment of the present invention provides an organic light emitting device, including: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound of any one of formulas 1 to 8.
The organic material layer of the organic light emitting device of the present invention may also be composed of a single layer structure, or may be composed of a multilayer structure in which two or more organic material 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 light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
In one exemplary embodiment of the present invention, the organic material layer comprises a hole injection layer, a hole transport layer, or a layer that simultaneously transports and injects holes, and the hole injection layer, the hole transport layer, or the layer that simultaneously transports and injects holes comprises the compound of formula 1.
In another exemplary embodiment, the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compound of formula 1.
According to an exemplary embodiment of the present invention, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound of any one of formulas 1 to 8.
In an exemplary embodiment of the present invention, the electron transport layer, the electron injection layer, or the layer that simultaneously transports and injects electrons comprises the compound of formula 1.
In another exemplary embodiment, the organic material layer includes a light emitting layer and an electron transporting layer, and the electron transporting layer includes a compound of any one of formulas 1 to 8.
In still another exemplary embodiment, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
In still another exemplary embodiment, the organic light emitting device may be an organic light emitting device having a reverse structure (inverted type) in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
For example, the structure of an organic light emitting device according to an exemplary embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In the structure, the compound may be included in the light emitting layer.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4. In the structure, the compound may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
The organic light emitting device of the present invention may be manufactured by materials and methods known in the art, except that one or more of the organic material layers comprises the compound of the present invention, i.e., the compound of any one of formulas 1 to 8.
When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
An exemplary embodiment of the present invention is an organic light emitting device comprising: a first electrode; a second electrode disposed to face the first electrode; a light-emitting layer disposed between the first electrode and the second electrode; and two or more organic material layers disposed between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the heterocyclic compound. In one exemplary embodiment, as the two or more organic material layers, two or more may be selected from an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, and a hole blocking layer.
In one exemplary embodiment of the present invention, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the heterocyclic compound. In particular, in one exemplary embodiment of the present invention, the heterocyclic compound may be further included in one of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
In addition, in one exemplary embodiment of the present invention, when the heterocyclic compound is included in each of the two or more electron transport layers, other materials than the heterocyclic compound may be the same as or different from each other.
The organic light emitting device of the present invention may be manufactured by materials and methods known in the art, except that one or more of the organic material layers includes the compound of any one of formulas 1 to 8, that is, the compound represented by any one of formulas 1 to 8.
For example, the organic light emitting device of the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device may be manufactured by: a metal or a metal oxide having conductivity or an alloy thereof is deposited on a substrate by using a Physical Vapor Deposition (PVD) method such as sputtering or electron beam evaporation to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and then a material usable as a cathode is deposited thereon. In addition to the above-described methods, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
Further, when an organic light emitting device is manufactured, the compound of any one of formulas 1 to 8 may be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method. Herein, the solution application method refers to spin coating, dip coating, doctor blade coating, ink jet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
In addition to the above-described method, the organic light emitting device may be manufactured by sequentially stacking a cathode material, an organic material layer, and an anode material on a substrate (international publication No. 2003/012890). However, the manufacturing method is not limited thereto.
In one exemplary embodiment of the invention, the first electrode is an anode and the second electrode is a cathode.
In another exemplary embodiment, 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 smoothly inject holes into the organic material layer. Specific examples of anode materials that can be used in the present invention include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals with oxides, e.g. ZnO, al or SnO 2 Sb; conductive polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxythiophene)](PEDOT), polypyrrole, polyaniline, and the like, but is not limited thereto.
As the cathode material, a material having a small work function is generally preferable in order to smoothly inject electrons into the organic material layer. Specific examples of the cathode material include: metals, e.g. magnesium, calcium, sodium,Potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multi-layer structured materials, e.g. LiF/Al or LiO 2 Al, etc., but is not limited thereto.
The hole injection material is a layer that injects holes from an electrode, and is preferably a compound having an ability to transport holes, and thus has an effect of injecting holes at an anode and an excellent effect of injecting holes for a light emitting layer or a light emitting material, prevents excitons generated from the light emitting layer from moving to the electron injection layer or the electron injection material, and is excellent in forming a thin film. Preferably, the Highest Occupied Molecular Orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine-based organic materials, hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyaniline, polythiophene-based conductive polymers, and the like, but are not limited thereto.
The electron transport material is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and the hole transport material is suitably a material that can receive holes from the anode or the hole injection layer to transfer holes to the light emitting layer, and has a large hole mobility. Specific examples thereof include arylamine organic materials, conductive polymers, block copolymers in which conjugated moieties are present together with non-conjugated moieties, and the like, but are not limited thereto.
The light emitting material is a material that can receive holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and combine the holes and electrons to emit light in the visible ray region, and is preferably a material having excellent quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxyquinoline aluminum complex (Alq 3); carbazole compounds; a dimeric styryl compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole, and benzimidazole compounds; poly (p-styrene) (PPV) based polymers; a spiro compound; polyfluorene, rubrene (rubrene), and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material. Examples of the host material include condensed aromatic ring derivatives or heterocyclic ring-containing compounds and the like. In particular, examples of the condensed aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic ring-containing compound include carbazole derivatives, dibenzofuran derivatives, ladder furan compounds, pyrimidine derivatives, and the like, but examples thereof are not limited thereto.
Examples of dopant materials include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. In particular, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and examples thereof include pyrene, anthracene having an arylamine group,
Figure BDA0001935808080000351
Bisindenopyrene, etc., and the styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group and one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and an arylamine group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styrylenediamine, styrylenetriamine, styrenetetramine, and the like. Further, examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the electron transport material is a material that can well receive electrons from the cathode and can transport electrons to the light emitting layer, and is suitably a material having a large electron mobility. Specific examples thereof include: al complex of 8-hydroxyquinoline; a complex comprising Alq 3; an organic radical compound; and hydroxyflavone-metal complexes, but are not limited thereto. The electron transport layer may be used with any desired cathode material, such as according to the related art. In particular, examples of suitable cathode materials are conventional materials with a low work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed 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 having an ability to transport electrons, has an excellent effect of injecting electrons from a cathode and injecting electrons into a light emitting layer or a light emitting material, prevents excitons generated from the light emitting layer from moving to a hole injection layer, and is excellent in forming a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone and its derivatives, metal complexes, nitrogen-containing five-membered derivatives, and the like, 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) chlorogallium, 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 device according to the present invention may be of a top emission type, a bottom emission type, or a double-sided emission type, depending on the materials used.
In one exemplary embodiment of the present invention, the compound of formula 1 may be contained in an organic solar cell or an organic transistor in addition to the organic light emitting device.
Mode for the invention
The preparation of the compound represented by formula 1 and the organic light emitting device including the same will be specifically described in the following examples. However, the following examples are provided to illustrate the invention and the scope of the invention is not limited thereto.
< preparation example >
< preparation example 1> [ preparation of Compound 1]
2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0 g,37.4 mmol) and 2- (2- (9, 9)-diphenyl-9H-fluoren-2-yl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan (19.4 g,37.4 mmol) was placed in 150ml THF. Into which 75ml of 2.0M K was placed 2 CO 3 And 0.8g Pd (PPh) 3 ) 4 The resulting mixture was then stirred and refluxed for 5 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized from chloroform and ethanol, thereby preparing [ Compound 1]](19.9 g, yield 85%, MS: [ M+H)] + ＝626)。
< preparation example 2> [ preparation of Compound 2]
2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0 g,37.4 mmol) and 2- (4- (9, 9' -spirobis [ fluorene)]-2-yl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan (19.4 g,37.4 mmol) was placed in 150ml THF. Into which 75ml of 2.0M K was placed 2 CO 3 And 0.8g Pd (PPh) 3 ) 4 The resulting mixture was then stirred and refluxed for 6 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized from chloroform and ethanol, thereby preparing [ compound 2](18.7 g, 80% yield, MS: [ M+H)] + ＝624)。
< preparation example 3> [ preparation of Compound 3]
2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0 g,37.4 mmol) and 2- (7- (9, 9-diphenyl-9H-fluoren-4-yl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan (19.4 g,37.4 mmol) were placed in 150ml THF. Into which 75ml of 2.0M K was placed 2 CO 3 And 0.8g Pd (PPh) 3 ) 4 The resulting mixture was then stirred and refluxed for 6 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized from chloroform and ethanol, thereby preparing [ compound 3]](18.0 g, 77% yield, MS: [ M+H)] + ＝626)。
< preparation example 4> [ preparation of Compound 5]
2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0 g,37.4 mmol) and 2- (3- (9, 9-diphenyl-9H-fluoren-2-yl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan (19.4 g,37.4 mmol) were placed in 150ml THF. Into which 75ml of 2.0M K is placed 2 CO 3 And 0.8gPd (PP)h 3 ) 4 The resulting mixture was then stirred and refluxed for 7 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized from chloroform and ethanol, thereby preparing [ compound 5] ]. (16.9 g, yield 72%, MS: [ M+H)] + ＝626)
< preparation example 5> [ preparation of Compound 7]
2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0 g,37.4 mmol) and 2- (2- (9, 9-diphenyl-9H-fluoren-2-yl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan (19.4 g,37.4 mmol) were placed in 150ml THF. Into which 75ml of 2.0M K is placed 2 CO 3 And 0.8gPd (PPh) 3 ) 4 The resulting mixture was then stirred and refluxed for 5 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized from chloroform and ethanol, thereby producing [ compound 7]. (17.8 g, 76% yield, MS: [ M+H)] + ＝626)
< preparation example 6> [ preparation of Compound 13]
2, 4-bis ([ 1,1' -biphenyl)]-4-yl) -6-chloro-1, 3, 5-triazine (10.0 g,23.8 mmol) and 2- (4- (9, 9-dimethyl-9H-fluoren-2-yl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan (9.4 g,23.8 mmol) were placed in 100ml THF. 50ml of 2.0M K was placed therein 2 CO 3 And 0.5g Pd (PPh) 3 ) 4 The resulting mixture was then stirred and refluxed for 5 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized from chloroform and ethanol, thereby producing [ compound 13]. (12.3 g, yield 79%, MS: [ M+H)] + ＝654)
< preparation example 7> [ preparation of Compound 27]
2-chloro-4, 6-bis (naphthalen-1-yl) -1,3, 5-triazine (10.0 g,27.2 mmol) and 2- (4- (9, 9-diphenyl-9H-fluoren-4-yl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan (14.7 g,27.2 mmol) were placed in 150ml THF. Into which 75ml of 2.0M K is placed 2 CO 3 And 0.6g Pd (PPh) 3 ) 4 The resulting mixture was then stirred and refluxed for 6 hours. The mixture was cooled to room temperature, and then the mixture was filtered to give a mixtureThe solid was recrystallized from chloroform and ethanol, thereby preparing [ Compound 27 ]]. (13.8 g, yield 70%, MS: [ M+H)] + ＝726)
< preparation example 8> [ preparation of Compound 32]
2-chloro-4, 6-bis (naphthalen-2-yl) -1,3, 5-triazine (10.0 g,27.2 mmol) and 2- (4- (9, 9' -spirobis [ fluorene)]-4-yl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan (14.1 g,27.2 mmol) was placed in 150ml THF. Into which 75ml of 2.0M K is placed 2 CO 3 And 0.6g Pd (PPh) 3 ) 4 The resulting mixture was then stirred and refluxed for 7 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized from chloroform and ethanol, thereby producing [ compound 32]. (15.0 g, 76% yield, MS: [ M+H)] + ＝724)
< preparation example 9> [ preparation of Compound 36]
2-chloro-4, 6-bis (phenanthren-9-yl) -1,3, 5-triazine (10.0 g,21.4 mmol) and 2- (4- (9, 9-dimethyl-9H-fluoren-1-yl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxapentaborane (8.5 g,21.4 mmol) were placed in 150ml THF. Into which 75ml of 2.0M K is placed 2 CO 3 And 0.5g Pd (PPh) 3 ) 4 The resulting mixture was then stirred and refluxed for 5 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized from chloroform and ethanol, thereby producing [ compound 36]. (11.6 g, yield 77%, MS: [ M+H)] + ＝702)
< preparation example 10> [ preparation of Compound 46]
2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0 g,37.4 mmol) and 2- (4 '- (9, 9-diphenyl-9H-fluoren-2-yl) - [1,1' -biphenyl)]-4-yl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan (22.3 g,37.4 mmol) was placed in 150ml THF. Into which 75ml of 2.0M K is placed 2 CO 3 And 0.8g Pd (PPh) 3 ) 4 The resulting mixture was then stirred and refluxed for 6 hours.
The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized from chloroform and ethanol, thereby producing [ compound 46]. (17.9 g, yield 68%, MS: [ M+H)] + ＝702)
< preparation example 11> [ preparation of Compound 47]
2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0 g,37.4 mmol) and 2- (4 '- (9, 9' -spirobis [ fluorene)]-2-yl) - [1,1' -biphenyl ]]-4-yl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan (22.2 g,37.4 mmol) was placed in 150ml THF. Into which 75ml of 2.0M K is placed 2 CO 3 And 0.8g Pd (PPh) 3 ) 4 The resulting mixture was then stirred and refluxed for 8 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized from chloroform and ethanol, thereby producing [ compound 47] ]. (21.2 g, yield 81%, MS: [ M+H)] + ＝700)
< preparation example 12> [ preparation of Compound 67]
2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0 g,37.4 mmol) and 2- (4 '- (9, 9-diphenyl-9H-fluoren-4-yl) - [1,1' -biphenyl)]-4-yl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan (22.3 g,37.4 mmol) was placed in 150ml THF. Into which 75ml of 2.0M K is placed 2 CO 3 And 0.8g Pd (PPh) 3 ) 4 The resulting mixture was then stirred and refluxed for 8 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized from chloroform and ethanol, thereby preparing [ compound 67]]. (18.6 g, 71% yield, MS: [ M+H)] + ＝702)
< preparation example 13> [ preparation of Compound 80]
2-chloro-4, 6-bis (phenyl-d 5) -1,3, 5-triazine (10.0 g,36.0 mmol) and 2- (4- (9, 9-diphenyl-9H-fluoren-4-yl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxapentaborane (18.7 g,36.0 mmol) were placed in 150ml THF. Into which 75ml of 2.0M K is placed 2 CO 3 And 0.8g Pd (PPh) 3 ) 4 The resulting mixture was then stirred and refluxed for 6 hours. The mixture was cooled to normal temperature, and then the solid produced by filtering the mixture was recrystallized from chloroform and ethanol, thereby producing [ compound 80]]. (16.0 g, yield 70%, MS: [ M+H)] + ＝636)
< example >
Example 1
Thin coating Indium Tin Oxide (ITO) to have
Figure BDA0001935808080000391
The glass substrate having a thickness is put into distilled water in which a cleaning agent is dissolved, and is subjected to ultrasonic cleaning. In this case, a product manufactured by Fischer co. Was used as a detergent, and distilled water filtered twice using a filter manufactured by Millipore co. Was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed twice using distilled water for 10 minutes. After the washing with distilled water was completed, ultrasonic washing was performed using isopropanol, acetone and methanol solvents, and drying was performed, and then the product was transferred to a plasma washer. In addition, the substrate was cleaned with oxygen plasma for 5 minutes and then transferred to a vacuum evaporator.
The following compound [ HI-A ] was taken]Thermal vacuum deposition onto transparent ITO electrode prepared as described above
Figure BDA0001935808080000392
Thereby forming a hole injection layer. The compound [ HAT ]]/>
Figure BDA0001935808080000393
And the following compounds [ HT-A ]]/>
Figure BDA0001935808080000394
Sequentially vacuum-depositing on the hole injection layer, thereby forming a hole transport layer.
Subsequently, the following compound [ BH ]]And compound [ BD ]]Vacuum deposited on the hole transport layer at a weight ratio of 25:1 to have
Figure BDA0001935808080000395
To form a light emitting layer.
Will [ Compound 1]]And the following compound [ LiQ ]](lithium quinolinate) is vacuum deposited on the light emitting layer in a 1:1 weight ratio to form a light emitting device having
Figure BDA0001935808080000396
Electron injection and transport layers of the thickness of (a). Subsequently lithium fluoride (LiF) and aluminum are deposited on the electron injection and transport layer to have +.>
Figure BDA0001935808080000397
And->
Figure BDA0001935808080000398
Thereby forming a cathode.
In the above step, the deposition rate of the organic material is maintained at
Figure BDA0001935808080000399
To->
Figure BDA00019358080800003910
The deposition rates of lithium fluoride and aluminum of the cathode are maintained at +.>
Figure BDA0001935808080000401
And->
Figure BDA0001935808080000402
And the vacuum degree during deposition is maintained at 1×10 -7 To 5X 10 -8 And a support, thereby manufacturing an organic light emitting device.
Figure BDA0001935808080000403
Example 2
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ compound 2] was used instead of [ compound 1] of [ example 1].
Example 3
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ compound 3] was used instead of [ compound 1] of [ example 1].
Example 4
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ compound 5] was used instead of [ compound 1] of [ example 1].
Example 5
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ compound 7] was used instead of [ compound 1] of [ example 1].
Example 6
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ compound 13] was used instead of [ compound 1] of [ example 1].
Example 7
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ compound 27] was used instead of [ compound 1] of [ example 1].
Example 8
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ compound 32] was used instead of [ compound 1] of [ example 1].
Example 9
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ compound 36] was used instead of [ compound 1] of [ example 1].
Example 10
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ compound 46] was used instead of [ compound 1] of [ example 1].
Example 11
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ compound 47] was used instead of [ compound 1] of [ example 1].
Example 12
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ compound 67] was used instead of [ compound 1] of [ example 1].
Example 13
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ compound 80] was used instead of [ compound 1] of [ example 1].
Comparative example 1
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ ET-a ] was used instead of [ compound 1] of [ example 1].
Comparative example 2
An organic light-emitting device was manufactured in the same manner as in [ example 1], except that [ ET-B ] was used instead of [ compound 1] of [ example 1].
For the organic light-emitting device manufactured by the above method, the temperature was set at 10mA/cm 2 The driving voltage and luminous efficiency were measured at a current density of 20mA/cm 2 Is measured at a current density of 90% of the initial luminance (T 90 ). The results are shown in table 1 below.
TABLE 1
Figure BDA0001935808080000431
According to the results of the table, the compound represented by formula 1 according to the present invention may be used for an organic layer of the organic light emitting device that can simultaneously inject and transport electrons. The organic light emitting device using the same has a low driving voltage and high efficiency, and the stability of the device can be improved by the hole stability of the compound.
In particular, the compound represented by formula 1 according to the present invention is excellent in effect in terms of thermal stability and can be used in a mixture with an n-type dopant when used in an organic layer for simultaneously injecting and transporting electrons.
Further, according to an exemplary embodiment of the present invention, the case in which the compound represented by formula 8 is used for an organic light emitting device has a lower driving voltage and/or higher efficiency, and the stability of the apparatus may be increased due to the hole stability of the compound, as compared to the case in which the compounds represented by formulas 5 to 7 are used for an organic light emitting device.
[ description of reference numerals ]
1: substrate
2: anode
3: light-emitting layer
4: cathode electrode
5: hole injection layer
6: hole transport layer
7: light-emitting layer
8: electron transport layer
The following corresponds to the original claims of the parent application:
1. a compound represented by the following formula 1:
[ 1]
Figure BDA0001935808080000441
In the formula (1) of the present invention,
ar1 and Ar2 are identical to each other and are phenyl, which is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfinyl groups, arylsulfinyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, arylphosphine groups, and heterocyclic groups; biphenyl, unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfinyl groups, arylsulfinyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, arylphosphine groups, and heterocyclic groups; naphthyl, which is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfinyl groups, arylsulfinyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, arylphosphine groups, and heterocyclic groups; or phenanthryl, which is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfinyl groups, arylsulfinyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, arylphosphine groups, and heterocyclic groups;
L is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,
r1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; a substituted or unsubstituted alkylsulfinyl group; a substituted or unsubstituted aryl sulfinyl group; a substituted or unsubstituted alkenyl group; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; a substituted or unsubstituted alkylamino group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroaryl amine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamino group; substituted or unsubstituted aryl phosphino; substituted or unsubstituted phosphine oxide groups; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group, or optionally combined with an adjacent group to form a substituted or unsubstituted ring,
R3 and R4 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; a substituted or unsubstituted alkylsulfinyl group; a substituted or unsubstituted aryl sulfinyl group; a substituted or unsubstituted alkenyl group; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; a substituted or unsubstituted alkylamino group; a substituted or unsubstituted aralkylamine group; substituted or unsubstituted aryl phosphino; or a substituted or unsubstituted phosphine oxide group; or optionally with adjacent groups to form a substituted or unsubstituted ring,
m is an integer of 1 to 5,
a is an integer of 0 to 3, and
b is an integer of 0 to 4, and
When m, a and b are each 2 or more, the structures in brackets are the same or different from each other.
2. The compound according to item 1, wherein formula 1 is represented by any one of the following formulas 2 to 4:
[ 2]
Figure BDA0001935808080000461
[ 3]
Figure BDA0001935808080000462
[ 4]
Figure BDA0001935808080000471
In the formulae 2 to 4,
ar1, ar2, L, R3, R4, a, b and m are as defined in formula 1,
r11, R12, R21 and R22 are as defined for R3 and R4,
x1 and X2 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; a substituted or unsubstituted alkylsulfinyl group; a substituted or unsubstituted aryl sulfinyl group; a substituted or unsubstituted alkenyl group; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; a substituted or unsubstituted alkylamino group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroaryl amine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamino group; substituted or unsubstituted aryl phosphino; or a substituted or unsubstituted phosphine oxide group; or optionally with adjacent groups to form a substituted or unsubstituted ring,
r11 and r12 are the same or different from each other and are each independently an integer of 0 to 5,
r21 and r22 are the same or different from each other and each independently is an integer of 0 to 4, and
when r11, r12, r21 and r22 are each 2 or more, the structures in brackets are the same or different from each other.
3. The compound according to item 1, wherein formula 1 is represented by any one of the following formulas 5 to 8:
[ 5]
Figure BDA0001935808080000481
[ 6]
Figure BDA0001935808080000482
[ 7]
Figure BDA0001935808080000483
[ 8]
Figure BDA0001935808080000491
In the formulae 5 to 8,
ar1, ar2, L, R1 to R4, m, a and b are as defined in formula 1.
4. The compound of item 1, wherein L is any one selected from the following structures:
Figure BDA0001935808080000492
/>
Figure BDA0001935808080000501
the structure is optionally unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio; arylthio; an alkylsulfinyl group; aryl sulfinyl; a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; and a heterocyclic group.
5. The compound according to item 1, wherein L is phenylene or biphenylene.
6. The compound of item 1, wherein Ar1 and Ar2 are the same as each other and are phenyl, which is unsubstituted or substituted with one or more substituents selected from deuterium and alkyl; biphenyl, which is unsubstituted or substituted with one or more substituents selected from deuterium, alkyl and aryl; naphthyl, which is unsubstituted or substituted with one or more substituents selected from deuterium, alkyl and aryl; or phenanthryl, which is unsubstituted or substituted with one or more substituents selected from deuterium, alkyl and aryl.
7. The compound of item 1, wherein R1 and R2 are the same or different from each other and are each independently alkyl; or aryl, which is unsubstituted or substituted with one or more substituents selected from deuterium, halogen groups, alkyl and alkoxy; or combine with each other to form a ring.
8. The compound of item 1, wherein R3 and R4 are hydrogen.
9. The compound according to item 1, wherein
Figure BDA0001935808080000502
The moiety is any one selected from the following structures: />
Figure BDA0001935808080000511
Figure BDA0001935808080000521
In the case of the construction described above, in which the first and second support members are arranged,
r1 and R2 are as defined in formula 1, and
the structure can be unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio; arylthio; an alkylsulfinyl group; aryl sulfinyl; a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; and a heterocyclic group.
10. The compound of item 1, wherein the compound of formula 1 is any one selected from the group consisting of:
Figure BDA0001935808080000522
/>
Figure BDA0001935808080000531
/>
Figure BDA0001935808080000541
/>
Figure BDA0001935808080000551
/>
Figure BDA0001935808080000561
/>
Figure BDA0001935808080000571
/>
Figure BDA0001935808080000581
/>
Figure BDA0001935808080000591
/>
Figure BDA0001935808080000601
Figure BDA0001935808080000611
11. an organic light emitting device comprising:
a first electrode;
a second electrode disposed to face the first electrode; and
one or more layers of organic material disposed between the first electrode and the second electrode,
wherein one or more of the layers of organic material comprises a compound according to any one of items 1 to 10.
12. The organic light-emitting device according to item 11, wherein the organic material layer containing the compound is a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes.
13. The organic light-emitting device according to item 11, wherein the organic material layer containing the compound is an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons.
14. The organic light-emitting device according to item 11, wherein the organic material layer containing the compound is a light-emitting layer.

Claims (6)

1. An organic light emitting device comprising:
a first electrode;
a second electrode disposed to face the first electrode; and
one or more layers of organic material disposed between the first electrode and the second electrode,
Wherein one or more of the organic material layers comprises a compound represented by the following formula 1:
[ 1]
Figure FDA0004051629410000011
In the formula (1) of the present invention,
ar1 and Ar2 are the same as each other and are phenanthryl;
l is phenylene or biphenylene, and is a group,
r1 and R2 are identical or different from each other and are each independently an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms,
r3 and R4 are hydrogen,
m is 1, and the number of m is 1,
a is an integer of 0 to 3, and
b is an integer of 0 to 4,
wherein the organic material layer containing the compound is an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons.
2. The organic light-emitting device according to claim 1, wherein formula 1 is represented by any one of the following formulas 2 or 4:
[ 2]
Figure FDA0004051629410000021
[ 4]
Figure FDA0004051629410000022
In the formulae 2 and 4,
ar1, ar2, L, R3, R4, a, b and m are as defined in formula 1,
r11 and R12 are as defined for R3 and R4,
x1 and X2 are identical or different from each other and are each independently an alkyl group having 1 to 20 carbon atoms,
r11 and r12 are the same or different from each other and are each independently an integer of 0 to 5.
3. The organic light-emitting device according to claim 1, wherein formula 1 is represented by any one of the following formulas 5 to 8:
[ 5]
Figure FDA0004051629410000031
[ 6]
Figure FDA0004051629410000032
[ 7]
Figure FDA0004051629410000033
[ 8]
Figure FDA0004051629410000041
In the formulae 5 to 8,
ar1, ar2, L, R1 to R4, m, a and b are as defined in formula 1.
4. The organic light-emitting device according to claim 1, wherein L is any one selected from the following structures:
Figure FDA0004051629410000042
Figure FDA0004051629410000051
5. the organic light-emitting device of claim 1, wherein the compound of formula 1 is any one selected from the group consisting of:
[ Compound 33]
Figure FDA0004051629410000061
Figure FDA0004051629410000071
6. The organic light-emitting device of claim 1, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer also comprises the compound.
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