CN107325090B - Compound and organic electronic element comprising same - Google Patents

Compound and organic electronic element comprising same Download PDF

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CN107325090B
CN107325090B CN201710235792.4A CN201710235792A CN107325090B CN 107325090 B CN107325090 B CN 107325090B CN 201710235792 A CN201710235792 A CN 201710235792A CN 107325090 B CN107325090 B CN 107325090B
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CN107325090A (en
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郑珉祐
李东勋
许瀞午
张焚在
姜敏英
许东旭
韩美连
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LG Chem Ltd
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Abstract

The present invention relates to a compound and an organic electronic element comprising the same. The compound of the present invention is used for an organic electronic device represented by an organic light emitting device, and can reduce the driving voltage of the organic electronic device, improve the light efficiency, and improve the life characteristics of the device by utilizing the thermal stability of the compound.

Description

Compound and organic electronic element comprising same
Technical Field
This application claims priority to korean patent application No. 10-2016-.
The present specification relates to compounds and organic electronic components comprising the same.
Background
An organic electronic element refers to an electronic element using an organic semiconductor material, which requires exchange of holes and/or electrons between an electrode and the organic semiconductor material. Organic electronic components can be broadly classified into the following two types according to the operation principle. The first is an electronic component of the following form: photons introduced from an external light source into the element form excitons (exiton) in the organic layer, the excitons are separated into electrons and holes, and the electrons and holes migrate to the other electrodes, respectively, and are used as a current source (voltage source). The second is an electronic component of the following form: a voltage or a current is applied to 2 or more electrodes, holes and/or electrons are injected into the electrodes and the organic semiconductor material layer constituting the interface, and the operation is performed by the injected electrons and holes.
Examples of the organic electronic element include an organic light emitting element, an organic solar cell, an Organic Photoreceptor (OPC), an organic transistor, and the like, and in order to drive the element, a substance for injecting or transporting a hole, a substance for injecting or transporting an electron, or a light emitting substance is required. Hereinafter, the organic light-emitting element will be mainly described in detail, but in the above-described organic electronic element, a substance for injecting or transporting a hole, a substance for injecting or transporting an electron, or a light-emitting substance operates on a similar principle.
In general, the organic light emission phenomenon is a phenomenon in which electric energy is converted into light energy by using an organic substance. An organic light emitting element utilizing an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer interposed therebetween. Among them, in order to improve efficiency and stability of the organic light emitting element, 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 element, if a voltage is applied between both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, an exciton (exiton) is formed when the injected holes and electrons meet, and light is emitted when the exciton falls back to the ground state.
There is a continuing need to develop new materials for use in organic light emitting elements as described above.
Documents of the prior art
Patent document
International patent application publication No. 2003-012890
Disclosure of Invention
The present specification provides a compound and an organic electronic element comprising the same.
One embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
Figure GDA0002356494730000021
In the chemical formula 1 described above,
a is S, P (Ar) or SiRR',
b is O or S, and B is O or S,
wherein, when A is S, B is O,
X1to X3At least 2 of them are N, the others are N or CR ",
L1is a substituted or unsubstituted arylene group,
Ar、Ar1and Ar2Are the same or different from each other, each independently hydrogen; deuterium; a halogen group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; a substituted or unsubstituted phosphine oxide group; substituted or unsubstituted aryl; or a substituted or unsubstituted heteroaryl group,
R、R’、R”、R1and R2Are the same or different from each other, 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 amide group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; a substituted or unsubstituted aryloxy group; substituted or unsubstituted alkylsulfoxy; substituted or unsubstituted arylsulfenoxy; a substituted or unsubstituted alkyl sulfoxide group; substituted or unsubstituted alkenyl; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; substitutionOr an unsubstituted phosphine oxide group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylamine group; substituted or unsubstituted aryl; or a substituted or unsubstituted heteroaryl group,
p is an integer of 1 to 3,
q is an integer of 1 to 4,
when p is 2 or more, plural R1Are the same as or different from each other,
when q is 2 or more, plural R2The same or different from each other.
Further, an embodiment of the present specification provides an organic electronic element including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include the compound of chemical formula 1.
The compound according to one embodiment of the present specification is used for an organic electronic device typified by an organic light-emitting device, and can reduce a driving voltage of the organic electronic device, improve light efficiency, and improve life characteristics of the device by utilizing thermal stability of the compound.
Drawings
Fig. 1 is a diagram illustrating an organic electronic element 10 according to an embodiment of the present specification.
Fig. 2 is a diagram illustrating an organic electronic element 11 according to another embodiment of the present specification.
FIG. 3 is a graph showing the MS DATA values of Compound 1.
FIG. 4 is a graph showing the MS DATA values of Compound 2.
FIG. 5 is a graph showing the MS DATA values of Compound 3.
FIG. 6 is a graph showing the MS DATA values of Compound 4.
FIG. 7 is a graph showing the MS DATA values of Compound 5.
Description of the symbols
10. 11: organic electronic component
20: substrate
30: a first electrode
40: luminescent layer
50: second electrode
60: hole injection layer
70: hole transport layer
80: electron blocking layer
90: electron transport layer
100: electron injection layer
Detailed Description
The present specification will be described in more detail below.
One embodiment of the present specification provides a compound represented by the above chemical formula 1.
Examples of the substituent in the present specification are described below, but not limited thereto.
In the context of the present specification,
Figure GDA0002356494730000041
refers to the location of the connection.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the position where the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means that the compound is selected from 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; an alkyl group; a cycloalkyl group; an alkenyl group; an amine group; a phosphine oxide group; an aryl group; a silyl group; and 1 or 2 or more substituents of the heterocyclic group containing 1 or more of N, O, S, Se and Si atoms, or a substituent linked by 2 or more substituents of the above-exemplified substituents, or no substituent.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the carbon number of the carbonyl group is not particularly limited, but a carbonyl group having 1 to 50 carbon atoms is preferable. Specifically, the compound may be a compound of the following structure, but is not limited thereto.
Figure GDA0002356494730000051
In the present specification, the number of carbon atoms of the ester group is not particularly limited, but an ester group having 1 to 50 carbon atoms is preferable. Specifically, the compound may be represented by the following structural formula, but is not limited thereto.
Figure GDA0002356494730000052
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but an imide group having 1 to 50 carbon atoms is preferable. Specifically, the compound may be a compound of the following structure, but is not limited thereto.
Figure GDA0002356494730000053
In the present specification, with respect to the amide group, the nitrogen of the amide group may be substituted with hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
Figure GDA0002356494730000061
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethyl-propyl group, 1-dimethyl-propyl group, 1-, Isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, 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, but is not limited thereto.
In the present specification, the alkoxy group may be a straight chain, a branched chain or a cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but an alkoxy group having 1 to 20 carbon atoms is preferable. Specifically, there may be mentioned methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy and the like, but not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples thereof include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-methyl-1-butenyl group, 1, 3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-diphenylvinyl-1-yl group, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl group, 2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group(s) ((s))
Figure GDA0002356494730000073
) And styryl group (
Figure GDA0002356494730000074
) And the like, but are not limited thereto.
In the present specification, the silyl group isThe substituent containing Si and directly bonded to the Si atom as a radical is represented by-SiR104R105R106，R104To R106The same or different from each other, each independently may be hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In this specification, the boron group may be-BR100R101R is as defined above100And R101The same or different from each other, each independently may be selected from hydrogen; deuterium; halogen; a nitrile group; 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, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but a monocyclic aryl group having 6 to 25 carbon atoms is preferable. Specifically, as the monocyclic aryl group, phenyl, biphenyl, terphenyl, tetrabiphenyl, and the like are possible, but not limited thereto.
In the case where the above-mentioned aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but a polycyclic aryl group having 10 to 24 carbon atoms is preferable. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
Figure GDA0002356494730000071
And fluorenyl, and the like, but are not limited thereto.
In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
When the fluorenyl group is substituted, it may be
Figure GDA0002356494730000072
Figure GDA0002356494730000081
Or
Figure GDA0002356494730000082
And the like, but are not limited thereto.
In the present specification, the heteroaryl group is a heterocyclic group containing N, O, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but is preferably a heteroaryl group having 2 to 60 carbon atoms. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,
Figure GDA0002356494730000083
Azolyl group,
Figure GDA0002356494730000084
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzopyrazinyl, pyrazinyl, triazinyl, pyrazinyl, carbazolyl, benzoxazolyl
Figure GDA0002356494730000085
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthroline, thiazolyl, and isoquinoyl
Figure GDA0002356494730000086
Azolyl group,
Figure GDA0002356494730000087
Oxadiazolyl, thiadiazolinyl, benzothiazolyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the "adjacent group" may represent a substituent substituted on an atom directly connected to an atom substituted with the relevant substituent, a substituent closest to the relevant substituent in terms of a steric structure, or another substituent substituted on an atom substituted with the relevant substituent. For example, 2 substituents on the phenyl ring substituted at the ortho (ortho) position and 2 substituents on the same carbon on the aliphatic ring may be interpreted as "adjacent groups" to each other.
In the present specification, the meaning that adjacent groups are bonded to each other to form a ring is that, as described above, adjacent groups are bonded to each other to form a 5-to 8-membered hydrocarbon ring or a 5-to 8-membered heterocyclic ring, which may be monocyclic or polycyclic, may be aliphatic, aromatic or a condensed form thereof, but is not limited thereto.
In the present specification, the term "amino group" means an amino group (-NH-)2) Is represented by-NR and a 1-valent amine in which at least one hydrogen atom of the group is substituted by another substituent107R108，R107And R108The same or different from each other, each independently may be at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group and a heterocyclic group (wherein, R is107And R108At least one of which is not hydrogen). For example, it may be selected from monoalkylamino groups, dialkylamino groups, N-alkylarylamino groups, monoarylamino groups, diarylamino groups, N-arylheteroarylamino groups, N-alkylheteroarylamino groups, monoheteroarylamino groups, and diheteroarylamino groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, a ditolylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-phenanthrenylfluorenylamino group, and an N-biphenylfluorenylamino.
In the present specification, the phosphine oxide group specifically includes, but is not limited to, diphenylphosphineoxide, dinaphthylphosphine oxide and the like.
In the present specification, the aryl group in the aryloxy group, the arylsulfenoxy group and the arylsulfoxide group is the same as the above-mentioned aryl group. Specifically, examples of the aryloxy group include, but are not limited to, phenoxy, p-tolyloxy, o-tolyloxy, 3, 5-dimethyl-phenoxy, 2,4, 6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthracenyloxy, 2-anthracenyloxy, 9-anthracenyloxy, 1-phenanthrenyloxy, 3-phenanthrenyloxy, and 9-phenanthrenyloxy, examples of the arylthioxy group include phenylthioxy, 2-methylphenylsulfenoxy, and 4-tert-butylphenylsulfenoxy, and examples of the arylsulfoxido group include phenylsulfoxido and p-tolylsulfoxido.
In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. Arylamine groups containing more than 2 aryl groups may contain monocyclic aryl groups, polycyclic aryl groups, or both monocyclic and polycyclic aryl groups. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group. Specific examples of arylamine groups include, but are not limited to, phenylamino, naphthylamino, biphenylamino, anthracenylamino, 3-methyl-phenylamino, 4-methyl-naphthylamino, 2-methyl-biphenylamino, 9-methyl-anthracenylamino, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, carbazolyl, and triphenylamino.
In the present specification, as examples of the heteroarylamino group, there are a substituted or unsubstituted monoheteroarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted triheteroarylamino group. Heteroarylamine groups comprising more than 2 heteroaryl groups may comprise monocyclic heteroaryl groups, polycyclic heteroaryl groups, or both monocyclic heteroaryl and polycyclic heteroaryl groups. For example, the heteroaryl group in the heteroarylamino group can be selected from the examples of the heteroaryl group.
In the present specification, the aromatic ring group may be monocyclic or polycyclic, and may be selected from the examples of the aryl group except for a group having a valence other than 1.
In the present specification, arylene means a group having two binding sites on an aryl group, that is, a 2-valent group. The aryl groups described above can be used as long as they are each a 2-valent group.
In the present specification, heteroarylene means a group having two binding sites on a heteroaryl group, i.e., a 2-valent group. The above description of heteroaryl groups can be used, except that they are each 2-valent groups.
In one embodiment of the present specification, chemical formula 1 may be represented by any one of chemical formulae 2 to 4 below.
[ chemical formula 2]
Figure GDA0002356494730000101
[ chemical formula 3]
Figure GDA0002356494730000102
[ chemical formula 4]
Figure GDA0002356494730000103
In the above-mentioned chemical formulas 2 to 4,
for A, B, X1To X3、L1、Ar1、Ar2、R1And R2P, q are the same as defined in the above chemical formula 1.
In one embodiment of the present specification, chemical formula 1 may be represented by any one of chemical formulae 5 to 19 below.
[ chemical formula 5]
Figure GDA0002356494730000111
[ chemical formula 6]
Figure GDA0002356494730000112
[ chemical formula 7]
Figure GDA0002356494730000113
[ chemical formula 8]
Figure GDA0002356494730000121
[ chemical formula 9]
Figure GDA0002356494730000122
[ chemical formula 10]
Figure GDA0002356494730000123
[ chemical formula 11]
Figure GDA0002356494730000131
[ chemical formula 12]
Figure GDA0002356494730000132
[ chemical formula 13]
Figure GDA0002356494730000133
[ chemical formula 14]
Figure GDA0002356494730000141
[ chemical formula 15]
Figure GDA0002356494730000142
[ chemical formula 16]
Figure GDA0002356494730000143
[ chemical formula 17]
Figure GDA0002356494730000151
[ chemical formula 18]
Figure GDA0002356494730000152
[ chemical formula 19]
Figure GDA0002356494730000153
In the above-mentioned chemical formulas 5 to 19,
for X1To X3、L1、Ar、Ar1、Ar2、R、R’、R1、R2P and q are the same as defined in the above chemical formula 1.
In one embodiment of the present specification, a is S, P (Ar) or SiRR'.
In one embodiment of the present specification, a is S.
In one embodiment of the present specification, a is p (ar).
In one embodiment of the present specification, a is p (Ph) and Ph is phenyl.
In one embodiment of the present specification, a is SiRR'.
In one embodiment of the present specification, B is O or S.
In one embodiment of the present specification, B is O.
In one embodiment of the present specification, B is S.
In one embodiment of the present specification, when a is S, B is O.
In one embodiment of the present specification, X1To X3More than 2 of them are N, and the rest are N or CR'.
In one embodiment of the present disclosure, X1 to X3 are N.
In one embodiment of the present specification, L1 is a substituted or unsubstituted arylene.
In one embodiment of the present specification, L1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted naphthylene group.
In one embodiment of the present specification, L1 is naphthylene substituted with aryl.
In one embodiment of the present specification, L1 is naphthylene substituted with phenyl.
In one embodiment of the present specification, L1 is naphthylene.
In one embodiment of the present specification, L1 is phenylene.
In one embodiment of the present specification, Ar1And Ar2Are the same or different from each other, each independently hydrogen; deuterium; a halogen group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; a substituted or unsubstituted phosphine oxide group; substituted or unsubstituted aryl; or a substituted or unsubstituted heteroaryl.
In one embodiment of the present specification, Ar1And Ar2The same or different from each other, each independently is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, Ar1And Ar2The same or different from each other, each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl groupSubstituted terphenyl, or substituted or unsubstituted naphthyl.
In one embodiment of the present specification, Ar1And Ar2The same or different from each other, each independently is a terphenyl group substituted with pyridine.
In one embodiment of the present specification, Ar1And Ar2Identical to or different from each other, are each independently phenyl, biphenyl, terphenyl or naphthyl.
In one embodiment of the present specification, Ar1And Ar2Is phenyl.
In one embodiment of the present specification, Ar1And Ar2The same or different from each other, and each independently is a substituted or unsubstituted heteroaryl group having 6 to 50 carbon atoms.
In one embodiment of the present specification, Ar1And Ar2The same or different from each other, each independently is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
In one embodiment of the present specification, Ar1And Ar2The same or different from each other, each independently is a carbazolyl group, a dibenzofuranyl group or a dibenzothiophenyl group.
In one embodiment of the present specification, R, R ', R', R1And R2Are the same or different from each other, 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 amide group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; a substituted or unsubstituted aryloxy group; substituted or unsubstituted alkylsulfoxy; substituted or unsubstituted arylsulfenoxy; a substituted or unsubstituted alkyl sulfoxide group; substituted or unsubstituted alkenyl; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylamine group; substituted or unsubstituted aryl; or a substituted or unsubstituted heteroaryl.
In one embodiment of the present specification，R”、R1And R2The same or different from each other, each independently hydrogen.
According to an embodiment of the present specification, the compound may be any one selected from the following structural formulae.
Figure GDA0002356494730000181
Figure GDA0002356494730000191
Figure GDA0002356494730000201
Figure GDA0002356494730000211
The compound according to one embodiment of the present specification can be produced by the following production method. Representative examples are described in the following production examples, and substituents may be added or deleted or positions of substituents may be changed as necessary. In addition, starting materials, reaction conditions, and the like may be changed based on techniques known in the art.
One embodiment of the present specification provides an organic electronic device including the above compound.
In one embodiment of the present specification, there is provided an organic electronic element including: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound.
In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the another member but also a case where another member exists between the two members.
In the present specification, when a part is referred to as "including" a certain component, it means that other components may be further included without excluding other components unless otherwise stated.
The organic layer of the organic electronic device in the present specification may have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, as a representative example of the organic electronic element of the present invention, the organic light emitting element 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, an electron blocking layer, and/or a hole blocking layer as an organic layer.
According to an embodiment of the present disclosure, the organic electronic element may be selected from an organic light emitting element, an organic phosphorescent element, an organic solar cell, an Organic Photoreceptor (OPC), and an organic transistor.
According to one embodiment of the present disclosure, the organic electronic device is an organic light emitting device.
In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.
In one embodiment of the present specification, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.
In one embodiment of the present disclosure, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.
In one embodiment of the present specification, the organic layer includes an electron blocking layer, and the electron blocking layer includes the compound.
In one embodiment of the present specification, the organic electronic device further includes 1 or 2 or more layers selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
In one embodiment of the present invention, the organic electronic device includes: a first electrode, a second electrode provided so as to face the first electrode, and a light-emitting layer provided between the first electrode and the second electrode; the organic light-emitting device includes 2 or more organic layers between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, and at least one of the 2 or more organic layers contains the compound. In one embodiment of the present specification, the 2 or more organic layers may be 2 or more selected from an electron transport layer, an electron injection layer, a layer which simultaneously transports electrons and injects electrons, and a hole blocking layer.
In one embodiment of the present specification, the organic layer includes 2 or more electron transport layers, and at least one of the 2 or more electron transport layers includes the compound. Specifically, in one embodiment of the present specification, 1 layer of the 2 or more electron transport layers may contain the compound, or 2 or more electron transport layers may contain the compound.
In one embodiment of the present specification, when the 2 or more electron transport layers each contain the compound, materials other than the compound may be the same or different from each other.
In one embodiment of the present specification, the organic layer further includes a hole injection layer or a hole transport layer of a compound containing an arylamino group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic layer including the compound.
In another embodiment, the organic electronic element may be an organic electronic element having a structure in which an anode, 1 or more organic layers, and a cathode (normal type) are sequentially stacked on a substrate.
In one embodiment of the present disclosure, when the organic layer including the compound is an electron transport layer, the electron transport layer may further include an n-type dopant. The n-type dopant may be an n-type dopant known in the art, and for example, a metal or a metal complex may be used. According to one example, the electron transport layer including a compound may further include LiQ.
In one embodiment of the present specification, when the electron transport layer further includes an n-type dopant in addition to the compound, a weight ratio of the compound to the n-type dopant may be 1:100 to 100: 1. Specifically, it may be 1:10 to 10: 1. More specifically, it may be 1: 1.
In one embodiment of the present specification, when the organic layer containing the compound is a light-emitting layer, the compound is used as a host of the light-emitting layer, and further contains a light-emitting dopant.
In another embodiment, the light emitting dopant includes a fluorescent dopant or a phosphorescent dopant, and the phosphorescent dopant includes an iridium (Ir) -based phosphorescent dopant.
In another embodiment, the phosphorescent dopant material comprises Ir (ppy)3Or (piq)2Ir(acac)。
In another embodiment, the concentration of the dopant may be 1 wt% to 90 wt%. Specifically, it may be 1 wt% to 10 wt%.
In another embodiment, the organic electronic element may be an inverted (inverted) organic electronic element in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.
For example, the structure of the organic electronic element in the present specification may have the structures shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates an example of the structure of an organic electronic element 10 in which a first electrode 30, a light-emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. Fig. 1 is an exemplary structure of an organic electronic device according to an embodiment of the present disclosure, and may further include another organic layer.
Fig. 2 illustrates an organic electronic device in which a first electrode 30, a hole injection layer 60, a hole transport layer 70, an electron blocking layer 80, a light emitting layer 40, an electron transport layer 90, an electron injection layer 100, 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 another organic layer.
When the organic electronic element includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
The organic electronic device of the present specification may be manufactured using materials and methods known in the art, except that 1 or more of the organic layers include the compound described above, i.e., the compound represented by chemical formula 1.
For example, the organic light-emitting element of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, the following can be made: an anode is formed by depositing metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a Physical Vapor Deposition (PVD) method such as sputtering or electron beam evaporation (e-beam evaporation), an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and a substance which can be used as a cathode is deposited on the organic layer. In addition to such a method, an organic light-emitting element may be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order.
In addition, with respect to the compound of chemical formula 1, in the manufacture of the organic light emitting element, the organic layer may be formed not only by a vacuum evaporation method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to the above method, an organic light-emitting element may be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (international patent application publication No. 2003/012890). However, the manufacturing method is not limited thereto.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
In another embodiment, the first electrode is a cathode and the second electrode is an anode.
As the anode material, a material having a large work function is generally preferred so that holes can be made smoothThe organic layer is advantageously implanted. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
As the cathode substance, a substance having a small work function is generally preferable so that electrons can be easily injected 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, or alloys thereof; LiF/Al or LiO2A multilayer structure such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: the organic light emitting device has an ability to transport holes, has a hole injection effect from an anode, has an excellent hole injection effect for a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from migrating to an electron injection layer or an electron injection material, and has excellent thin film forming ability. Preferably, the Highest Occupied Molecular Orbital (HOMO) of the hole injecting species is between the work function of the anode species and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The electron blocking layer is a layer that prevents holes injected from the hole injection layer from passing through the light-emitting layer and entering the electron injection layer, and can improve the life and efficiency of the element.
The light-emitting substance of the light-emitting layer is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having a high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimerized styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (b) is
Figure GDA0002356494730000261
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylenevinylene) (PPV) based polymers; spiro (spiro) compounds; a polyfluorene; and rubrene, but not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds and the like. Specifically, the aromatic fused ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include compounds represented by the above chemical formula 1, dibenzofuran derivatives, and ladder-type furan compounds (A), (B), (C), (
Figure GDA0002356494730000262
) And pyrimidine derivatives, and the like, but are not limited thereto.
Examples of the dopant include aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene having an arylamino groupAnthracene,
Figure GDA0002356494730000271
Diindenoperene (Periflanthene) and the like, as the styrylamine compound, a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and includes a compound substituted with 1 or 2 or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino or unsubstituted, and the like. Specifically, it includes, but is not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. Further, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport layer is a substance that can favorably receive electrons from the cathode and transfer the electrons to the light-emitting layer. Specific examples include 8-hydroxyquinoline Al complexes; comprising Alq3The complex of (1); an organic radical compound; and hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the prior art. In particular, examples of suitable cathode substances are the usual substances having a low work function and associated with an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, samarium, and the like are included, and each of these substances is accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer for injecting electrons from the electrode, and the following compounds are preferred: has an ability to transport electrons, and has an electron injection effect from a cathode and an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and is excellent in thin-film formability. Specifically, they include fluorenones, anthraquinodimethanes, diphenoquinones, thiopyran dioxides, and mixtures thereof,
Figure GDA0002356494730000272
Azole,
Figure GDA0002356494730000273
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, etc. and derivatives thereof, metal complexes, and nitrogen-containing 5-membered ring derivatives, etc., but not limited thereto.
Examples of the metal complex include, but are not limited to, lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium bis (2-methyl-8-quinolinolato) chloride, gallium bis (2-methyl-8-quinolinolato) (o) gallium, aluminum bis (2-methyl-8-quinolinolato) (1-naphthol), and gallium bis (2-methyl-8-quinolinolato) (2-naphthol).
The hole-blocking layer is a layer that prevents holes from reaching the cathode, and can be formed under the same conditions as those of the hole-injecting layer. Specifically, comprise
Figure GDA0002356494730000274
An oxadiazole derivative or a triazole derivative, a phenanthroline derivative, Bathocuproine (BCP), an aluminum complex (aluminum complex), and the like, but is not limited thereto.
The organic light-emitting element according to one embodiment of the present specification may be of a front light-emitting type, a rear light-emitting type, or a both-side light-emitting type, depending on a material used.
The compound of the present specification can be applied to an organic electronic device typified by an organic phosphorescent device, an organic solar cell, an Organic Photoreceptor (OPC), an organic transistor, and the like by a principle similar to that in the case of applying the compound to an organic light-emitting device.
Hereinafter, the present specification will be described in detail with reference to examples. However, the embodiments of the present description may be modified into various other forms, and the scope of the present description is not to be construed as being limited to the embodiments described in detail below. The embodiments of the present description are provided to more fully describe the present description to those skilled in the art.
< production example >
< Synthesis example 1> -production of intermediates 1 to 8
(1) Production of intermediate 1
Figure GDA0002356494730000281
After heating the compound of the above chemical formula 1A (340.0g, 2.0mol) to 80 ℃ to 90 ℃, sulfur (sulfur) (64g, 2.0mol) was added in a solid state while stirring. Thereafter, aluminum chloride (AlCl) was added at 70 deg.C3) (133.3g, 1mol) was gradually charged 3 times, and then reacted at 100 ℃ for 4 hours. After that, a diluted hydrochloric acid solution was added to complete the reaction, and the reaction solution was extracted with 1L of chloroform, and then dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure to remove the unchanged chemical formula 1A, a solid was produced from ethanol, and then, intermediate 1(115g, 29%) was produced by filtration and drying.
(2) Production of intermediate 2
Figure GDA0002356494730000291
Formula 1A (100.0g, 587.51mmol) was added to 1000mL of tetrahydrofuran and cooled to-78 ℃. Then, n-butyllithium (n-BuLi) (470mL, 1175.02mmol) was slowly added dropwise over 1 hour with stirring, and after 1 hour of reaction, the temperature was raised to room temperature and the reaction was continued for 2 hours. After cooling to-78 ℃ again, dichloro (phenyl) phosphine (105g, 587.51mmol) was slowly added. After that, the reaction was further carried out for 2 hours, and then slowly warmed to room temperature and reacted for 4 hours. After the reaction, water was added to complete the reaction, and the aqueous layer and the organic layer were separated, and the organic layer was distilled under reduced pressure and extracted with chloroform (1L)/water (1L). The solution was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure, and then chemical formula 1A which did not change was removed, and after a solid was produced from ethanol, intermediate 2(71g, 44%) was produced by filtration and drying.
(3) Production of intermediate 3
Figure GDA0002356494730000292
Formula 1A (100.0g, 587.51mmol) was added to 1000mL of Tetrahydrofuran (THF) and cooled to-78 deg.C. Then, n-butyllithium (n-BuLi) (470mL, 1175.02mmol) was slowly added dropwise over 1 hour with stirring, and after 1 hour of reaction, the temperature was raised to room temperature and the reaction was continued for 2 hours. After cooling to-78 ℃ again, dichlorodimethylsilane (75.8g, 587.51mmol) was slowly poured in. After that, the reaction was further carried out for 2 hours, and then slowly warmed to room temperature and reacted for 4 hours. After the reaction, water was added to complete the reaction, and the aqueous layer and the organic layer were separated, and the organic layer was distilled under reduced pressure, extracted with chloroform (1L)/water (1L), and the solution was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure to remove the unchanged chemical formula 1A, a solid was produced using ethanol, and then, intermediate 3(68g, 51%) was produced by filtration and drying.
(4) Production of intermediate 4
Figure GDA0002356494730000301
Intermediate 1(30g, 145mmol) was added to 300mL Tetrahydrofuran (THF) and cooled to-78 deg.C. Then, n-butyllithium (n-BuLi) (72mL, 180mmol) was slowly added dropwise over 1 hour with stirring, and after 1 hour of reaction, the temperature was raised to room temperature and the reaction was continued for 2 hours. After that, the reaction mixture was cooled again to-78 ℃ and triisopropyl borate (33.8g, 180mmol) was slowly charged. After that, the reaction was further carried out for 2 hours, and then slowly warmed to room temperature and reacted for 4 hours. After the reaction, diluted hydrochloric acid (HCl) was added to complete the reaction, and then, an aqueous layer and an organic layer were separated, and the organic layer was distilled under reduced pressure and extracted with chloroform (1L)/water (1L). After the solution was dried over magnesium sulfate, the organic layer was distilled under reduced pressure, and then intermediate 4(25g, 68%) was produced using hexane.
(5) Production of intermediate 5
Figure GDA0002356494730000302
Figure GDA0002356494730000311
Intermediate 2(30g, 108mmol) was added to 300mL Tetrahydrofuran (THF) and cooled to-78 deg.C. Then, n-butyllithium (n-BuLi) (52mL, 130mmol) was slowly added dropwise over 1 hour with stirring, and after 1 hour of reaction, the temperature was raised to room temperature and the reaction was continued for 2 hours. After that, the reaction mixture was cooled again to-78 ℃ and triisopropyl borate (24.5g, 130mmol) was slowly charged. After that, the reaction was further carried out for 2 hours, and then slowly warmed to room temperature and reacted for 4 hours. After the reaction, diluted hydrochloric acid (HCl) was added to complete the reaction, and then, an aqueous layer and an organic layer were separated, and the organic layer was distilled under reduced pressure and extracted with chloroform (1L)/water (1L). After the solution was dried over magnesium sulfate, the organic layer was distilled under reduced pressure, and then intermediate 5(25g, 71%) was produced using hexane.
(6) Production of intermediate 6
Figure GDA0002356494730000312
Intermediate 3(30g,130mmol) was added to 300mL Tetrahydrofuran (THF) and cooled to-78 deg.C. Then, n-butyllithium (n-BuLi) (63mL, 156mmol) was slowly added dropwise over 1 hour with stirring, and after 1 hour of reaction, the temperature was raised to room temperature and the reaction was continued for 2 hours. After that, the reaction mixture was cooled again to-78 ℃ and triisopropyl borate (29.4g, 156mmol) was slowly charged. After that, the reaction was further carried out for 2 hours, and then slowly warmed to room temperature and reacted for 4 hours. After the reaction, diluted hydrochloric acid (HCl) was added to complete the reaction, and then, an aqueous layer and an organic layer were separated, and the organic layer was distilled under reduced pressure and extracted with chloroform (1L)/water (1L). This solution was dried over magnesium sulfate, and the organic layer was distilled under reduced pressure to obtain intermediate 6(26g, 74%) from hexane.
(7) Production of intermediate 7
Figure GDA0002356494730000321
The above chemical formula 7A (30.0g, 135mmol) and chemical formula 7B (59g, 135mmol) were added to 300mL of Tetrahydrofuran (THF) under a nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (K)2CO3) (37.2g, 269mmol) was dissolved in 100mL of water and charged, followed by tetrakis triphenylphosphine palladium (4.7g, 4.03mmol) after stirring well. After 12 hours of reaction, the temperature was lowered to normal temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After that, the organic layer was distilled under reduced pressure and then recrystallized from ethanol. The resulting solid was filtered and dried to produce intermediate 7(28g, 80%).
(8) Production of intermediate 8
Figure GDA0002356494730000322
Intermediate 7(28g, 62.01mmol) was added to 300mL of Acetonitrile (AN) under a nitrogen atmosphere, and potassium carbonate (K) was added with stirring2CO3) (17.1g, 124mmol) and 50mL of water were mixed and added. Thereafter, the mixture was heated in a water bath, and 1-Butanesulfonyl fluoride (1-Butanesulfonyl fluoride) (28.1g, 93mmol) was slowly added thereto. Thereafter, the reaction was terminated after about 1 hour. After completion of the reaction, the temperature was lowered to room temperature, and then the aqueous layer and the organic layer were separated, and the organic layer was distilled under reduced pressure to produce intermediate 8(41.1g, 91%).
< Synthesis example 2> -production of Compound 1
Figure GDA0002356494730000331
Intermediate 8(20.0g, 27mmol) and intermediate 4(6.7g, 27mmol) were placed in 200mL of Tetrahydrofuran (THF) under nitrogen, stirred and refluxed. Then, potassium carbonate (K)2CO3) (7.5g, 54.5mmol) was dissolved in 30mL of water and charged, and after stirring sufficiently, palladium tetrakistriphenylphosphine (0.9g, 0.8mmol) was charged. After 6 hours of reaction, the temperature was adjustedCooling to normal temperature and filtering. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized from ethyl acetate. The resulting solid was filtered and dried to produce compound 1(9.3g, 54%). Fig. 3 below is a graph showing the MS DATA value of compound 1.
MS：[M+H]+＝709
< Synthesis example 3> -production of Compound 2
Figure GDA0002356494730000341
Intermediate 8(20.0g, 27mmol) and intermediate 5(8.7g, 27mmol) were added to 200mL of Tetrahydrofuran (THF) under nitrogen, stirred and refluxed. Then, potassium carbonate (K)2CO3) (7.5g, 54.5mmol) was dissolved in 30mL of water and then charged, followed by stirring well and then tetrakis triphenylphosphine palladium (0.9g, 0.8mmol) was charged. After 6 hours of reaction, the temperature was lowered to normal temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After that, the organic layer was distilled under reduced pressure and recrystallized from ethyl acetate. The resulting solid was filtered and dried to produce compound 2(10.3g, 53%). Fig. 4 described below is a graph showing the MS DATA value of compound 2.
MS：[M+H]+＝659
< Synthesis example 4> -production of Compound 3
Figure GDA0002356494730000351
Intermediate 8(20.0g, 27mmol) and intermediate 6(8.7g, 27mmol) were added to 200mL of Tetrahydrofuran (THF) under nitrogen, stirred and refluxed. Then, potassium carbonate (K)2CO3) (7.5g, 54.5mmol) was dissolved in 30mL of water and then charged, followed by stirring well and then tetrakis triphenylphosphine palladium (0.9g, 0.8mmol) was charged. After 6 hours of reaction, the temperature was lowered to normal temperature and filtered. The filtrate was washed with chloroform andafter the water extraction, the organic layer was dried over magnesium sulfate. After that, the organic layer was distilled under reduced pressure and recrystallized from ethyl acetate. The resulting solid was filtered and dried to produce compound 3(11g, 61%). Fig. 5 is a graph showing the MS DATA value of compound 3.
MS：[M+H]+＝633
< Synthesis example 5> -production of Compound 4
Figure GDA0002356494730000352
Figure GDA0002356494730000361
Intermediate 8A (20.0g, 27mmol) produced by the same method as in the above intermediate 8 synthesis example and intermediate 4(6.7g, 27mmol) were added to 200mL of Tetrahydrofuran (THF) under a nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (K)2CO3) (7.5g, 54.5mmol) was dissolved in 30mL of water and charged, and after stirring sufficiently, palladium tetrakistriphenylphosphine (0.9g, 0.8mmol) was charged. After 6 hours of reaction, the temperature was lowered to normal temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After that, the organic layer was distilled under reduced pressure and recrystallized from ethyl acetate. The resulting solid was filtered and dried to produce compound 4(12.3g, 71%). Fig. 6 described below is a graph showing the MS DATA value of compound 4.
MS：[M+H]+＝633
<Synthesis example 6>Of Compound 5 (c)
Figure GDA0002356494730000363
) Manufacture of
Figure GDA0002356494730000362
Under nitrogen atmosphere, will utilize the intermediateIntermediate 8B (20.0g, 27mmol) and intermediate 4(6.7g, 27mmol), prepared in the same manner as in the synthesis example of fig. 8, were added to 200mL of tetrahydrofuran, followed by stirring and refluxing. Then, potassium carbonate (K)2CO3) (7.5g, 54.5mmol) was dissolved in 30mL of water and then charged, followed by stirring well and then tetrakis triphenylphosphine palladium (0.9g, 0.8mmol) was charged. After 6 hours of reaction, the temperature was lowered to normal temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After that, the organic layer was distilled under reduced pressure and recrystallized from ethyl acetate. The resulting solid was filtered and dried to produce compound 5(7.6g, 44%). Fig. 7 is a graph showing the MS DATA value of compound 5.
MS：[M+H]+＝633
< example >
< Experimental examples 1-1>
Will be provided with
Figure GDA0002356494730000371
A glass substrate (corning 7059 glass) coated with Indium Tin Oxide (ITO) in a thick film was placed in distilled water in which a dispersant was dissolved, and washed by ultrasonic waves. The detergent used was a product of fisher corporation (Fischer Co.) and the distilled water was filtered 2 times using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating 2 times with distilled water. After the completion of the distilled water washing, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, and then dried.
On the ITO transparent electrode thus prepared
Figure GDA0002356494730000372
The thickness of (a) was measured by thermal vacuum evaporation of hexanitrile Hexaazatriphenylene (HAT) to form a hole injection layer. Vacuum evaporating HT 1 as a hole transporting substance on the hole injection layer
Figure GDA0002356494730000373
Then, in order
Figure GDA0002356494730000374
The host H1 and the dopant D1 compound were vacuum-evaporated to a thickness of (1) to form a light-emitting layer. Compound 1 produced in example 2 and Lithium quinolinate (LiQ) were synthesized on the light-emitting layer by vacuum evaporation at a weight ratio of 1:1, and
Figure GDA0002356494730000375
the electron injection and transport layer is formed with a thickness of (1). On the electron injection and transport layer in turn
Figure GDA0002356494730000376
Depositing lithium fluoride (LiF) in a thickness of
Figure GDA0002356494730000377
The cathode is formed by depositing aluminum to a certain thickness, thereby manufacturing the organic light emitting element.
In the above process, the evaporation rate of the organic material is maintained at 0.4-0.4
Figure GDA0002356494730000378
Lithium fluoride maintenance of cathode
Figure GDA0002356494730000379
Deposition rate of (3), aluminum maintenance
Figure GDA00023564947300003710
The deposition rate of (2) and the degree of vacuum during deposition were maintained at 2X 10-7torr to 5X 10-6torr。
[HAT]
Figure GDA00023564947300003711
[LiQ]
Figure GDA0002356494730000381
[HT 1]
Figure GDA0002356494730000382
[H1]
Figure GDA0002356494730000383
[D1]
Figure GDA0002356494730000384
< Experimental examples 1 and 2>
An experiment was performed in the same manner as in experimental example 1-1 except that compound 2 was used instead of compound 1 as the electron transport layer.
< Experimental examples 1 to 3>
An experiment was performed in the same manner as in experimental example 1-1 except that compound 3 was used instead of compound 1 as the electron transport layer.
< Experimental examples 1 to 4>
An experiment was performed in the same manner as in experimental example 1-1 except that compound 4 was used instead of compound 1 as the electron transport layer.
< Experimental examples 1 to 5>
An experiment was performed in the same manner as in experimental example 1-1 except that compound 5 was used instead of compound 1 as the electron transport layer.
< Experimental example 2-1> -light-emitting layer (EML) example
Will be provided with
Figure GDA0002356494730000391
The glass substrate having a thin film coated with Indium Tin Oxide (ITO) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, a product of fisher corporation (Fischer Co.) was used as the detergent, and a Filter (Filter) manufactured by Millipore corporation (Millipore Co.) was used as the distilled water for filtrationDistilled water after 2 times. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating 2 times with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaning machine. Then, the substrate was cleaned with oxygen plasma for 5 minutes, and then transferred to a vacuum evaporator.
On the ITO transparent electrode thus prepared
Figure GDA0002356494730000392
The hole injection layer was formed by thermally vacuum-evaporating hexanitrile Hexaazatriphenylene (HAT) of the following chemical formula.
[HAT]
Figure GDA0002356494730000393
On the hole injection layer
Figure GDA0002356494730000394
The hole transport layer was formed by thermally vacuum-depositing an N, N-Bis- (1-naphthyl) -N, N-Bis-phenyl- (1,1-biphenyl) -4,4-diamine (N, N-Bis- (1-naphthyl) -N, N-Bis-phenyl- (1,1-biphenyl) -4,4-diamine, NPB) compound having the following structure.
[NPB]
Figure GDA0002356494730000401
Then, the hole transport layer is formed to have a film thickness
Figure GDA0002356494730000402
Compound 1(90 wt%) produced in Synthesis example 2 described above as a host, and 10 wt% Ir (ppy) as a dopant were vacuum-deposited3Thereby forming a light emitting layer. On the above-mentioned luminescent layer
Figure GDA0002356494730000403
The electron injecting and transporting layer is formed by vacuum evaporation of the following electron transporting material.
[ Electron transporting substance ]
Figure GDA0002356494730000404
On the electron injection and transport layer in turn
Figure GDA0002356494730000405
Depositing lithium fluoride (LiF) in a thickness of
Figure GDA0002356494730000406
Aluminum is evaporated to a thickness to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Figure GDA0002356494730000407
To
Figure GDA0002356494730000408
Lithium fluoride maintenance of cathode
Figure GDA0002356494730000409
Deposition rate of (3), aluminum maintenance
Figure GDA00023564947300004010
The deposition rate of (2) and the degree of vacuum during deposition were maintained at 2X 10-7torr to 5X 10-8torr。
< Experimental examples 2-2>
An experiment was performed in the same manner as in experimental example 2-1 except that compound 2 was used as the light-emitting layer instead of compound 1.
< Experimental examples 2 to 3>
An experiment was performed in the same manner as in experimental example 2-1 except that compound 3 was used as the light-emitting layer instead of compound 1.
< Experimental examples 2 to 4>
An experiment was performed in the same manner as in experimental example 2-1 except that compound 4 was used as the light-emitting layer instead of compound 1.
< Experimental examples 2 to 5>
An experiment was performed in the same manner as in experimental example 2-1 except that compound 5 was used as the light-emitting layer instead of compound 1.
< comparative example 1-1>
An organic light-emitting element was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, a compound of ET 1 described below was used instead of compound 1.
[ET 1]
Figure GDA0002356494730000411
< comparative examples 1 and 2>
An organic light-emitting element was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound of ET 2 described below was used instead of compound 1.
[ET 2]
Figure GDA0002356494730000421
< comparative example 2-1>
An organic light-emitting device was produced in the same manner as in experimental example 2-1, except that in experimental example 2-1, a compound of EM 1 described below was used instead of compound 1.
[EM 1]
Figure GDA0002356494730000422
Organic light-emitting devices manufactured using the respective compounds of the above experimental examples 1-1 to 1-5 as electron transport layer substances were controlled at 10mA/cm2The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm2Measured at a current density of 95% of the initial brightnessTime (LT 95). The results are shown in table 1 below.
[ Table 1]
Figure GDA0002356494730000431
Further, organic light-emitting devices manufactured using the respective compounds of the above experimental examples 2-1 to 2-5 as light-emitting layer substances were controlled at 10mA/cm2The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm2The time until 95% of the initial brightness was reached was measured at the current density of (LT 95). The results are shown in table 2 below.
[ Table 2]
Figure GDA0002356494730000432
Further, the organic light-emitting devices manufactured using the compounds of comparative examples 1-1 and 1-2 as electron transporting layer materials and the organic light-emitting devices manufactured using the compound of comparative example 2-1 as light-emitting layer material were each set at 10mA/cm2The drive voltage and the luminous efficiency were measured at the current density of (2). Furthermore, at 20mA/cm2The time until 95% of the initial brightness was reached was measured at the current density of (LT 95). The results are shown in table 3 below.
[ Table 3]
Figure GDA0002356494730000441
From the results of the above experimental examples and comparative examples, it is understood that when the compounds 1 to 5 described in the present specification are used as an electron transporting layer material, an organic light emitting element having high efficiency and life and low driving voltage can be manufactured as compared with the comparative examples 1-1 and 1-2 in which the compounds described in the present specification are not used. Further, it is found that in the case where the compounds 1 to 5 are used as the light emitting layer substance, excellent characteristics are exhibited in terms of efficiency and lifetime as compared with the substance of comparative example 2-1.
The preferred embodiments of the present invention have been described above, but the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the scope of the embodiments of the present invention, which also fall within the scope of the present invention.

Claims (8)

1. A compound selected from any one of the following compounds:
Figure FDA0002723586900000011
Figure FDA0002723586900000021
Figure FDA0002723586900000031
Figure FDA0002723586900000041
2. an organic electronic component, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound according to claim 1.
3. The organic electronic element according to claim 2, wherein the organic layer comprises a light-emitting layer containing the compound.
4. The organic electronic element according to claim 2, wherein the organic layer comprises a hole injection layer or a hole transport layer containing the compound.
5. The organic electronic element according to claim 2, wherein the organic layer comprises an electron injection layer or an electron transport layer comprising the compound.
6. The organic electronic element according to claim 2, wherein the organic layer comprises an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the compound.
7. The organic electronic element according to claim 2, wherein the organic electronic element further comprises 1 or 2 or more layers selected from a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.
8. The organic electronic element according to claim 2, wherein the organic electronic element is selected from the group consisting of an organic light-emitting element, an organic phosphorescent element, an organic solar cell, an organic photoreceptor, and an organic transistor.
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