CN113994495A - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- CN113994495A CN113994495A CN202080041475.9A CN202080041475A CN113994495A CN 113994495 A CN113994495 A CN 113994495A CN 202080041475 A CN202080041475 A CN 202080041475A CN 113994495 A CN113994495 A CN 113994495A
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- 239000000126 substance Substances 0.000 claims abstract description 163
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- NQFOGDIWKQWFMN-UHFFFAOYSA-N phenalene Chemical compound C1=CC([CH]C=C2)=C3C2=CC=CC3=C1 NQFOGDIWKQWFMN-UHFFFAOYSA-N 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- AMIGYDGSJCJWSD-UHFFFAOYSA-N thiocane Chemical compound C1CCCSCCC1 AMIGYDGSJCJWSD-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical group [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
The present specification provides an organic light emitting device including a compound represented by chemical formula 1 and a compound represented by chemical formula 2.
Description
Technical Field
This application claims priority to korean patent application No. 10-2019-0099429, filed by 14.8.2019, to the korean patent office, the entire contents of which are incorporated herein by reference.
The present description relates to organic light emitting devices.
Background
The organic light emitting device has a structure in which an organic thin film is disposed between 2 electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the 2 electrodes are combined in the organic thin film to be paired, and then quenched and emitted. The organic thin film may be formed of a single layer or a plurality of layers as necessary.
As a substance used in an organic light-emitting device, a pure organic substance or a complex compound of an organic substance and a metal is mainly used, and can be classified into a hole injecting substance, a hole transporting substance, a light-emitting substance, an electron transporting substance, an electron injecting substance, and the like according to the use. Here, as the hole injecting substance or the hole transporting substance, an organic substance having a p-type property, that is, an organic substance which is easily oxidized and has an electrochemically stable state at the time of oxidation is mainly used. On the other hand, as the electron injecting substance or the electron transporting substance, an organic substance having an n-type property, that is, an organic substance which is easily reduced and has an electrochemically stable state at the time of reduction is mainly used. The light-emitting layer material is preferably a material having both p-type and n-type properties, that is, a material having a stable form in both an oxidized state and a reduced state, and is preferably a material having high light emission efficiency in which holes and electrons are recombined in the light-emitting layer to generate excitons (exitons) which are converted into light.
In order to improve the performance, lifetime, or efficiency of organic light emitting devices, development of materials for organic thin films is continuously required.
Documents of the prior art
(patent document 1) Korean patent laid-open publication No. 10-2006-0009932
Disclosure of Invention
Technical subject
In this specification, an organic light-emitting device having a low driving voltage, high efficiency, or long life characteristics is described.
Means for solving the problems
An embodiment of the present specification provides an organic light emitting device including:
a first electrode;
a second electrode;
a light-emitting layer provided between the first electrode and the second electrode;
a first organic material layer provided between the first electrode and the light-emitting layer; and
a second organic layer disposed between the second electrode and the light-emitting layer,
the first organic layer includes a compound represented by the following chemical formula 1,
the second organic layer includes a compound represented by the following chemical formula 2.
[ chemical formula 1]
In the above-described chemical formula 1,
ar1 and Ar2, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
r1 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or adjacent groups may be bonded to each other to form a ring,
n is an integer of 1 to 8, and when n is 2 or more, R1 may be the same or different from each other,
[ chemical formula 2]
In the above-described chemical formula 2,
l is a direct bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkoxy group having a valence of 2, a substituted or unsubstituted alkenyl group having a valence of 2, or a substituted or unsubstituted heteroarylene group,
ar3 and Ar4, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted arylalkyl, a substituted or unsubstituted arylalkenyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl,
x1 is N or CR11, X2 is N or CR12, X3 is N or CR13,
at least one of X1 to X3 is N,
r11 to R13 are the same as or different from each other, and each independently is hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester group, imide group, amide group, substituted or unsubstituted Alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group (Alkyl thio), substituted or unsubstituted arylthio group (Aryl thio), substituted or unsubstituted alkylsulfonyl group (Alkyl sulfo xy), substituted or unsubstituted arylsulfonyl group (Aryl sulfo xy), substituted or unsubstituted alkenyl group, substituted or unsubstituted silyl group, substituted or unsubstituted boryl group, substituted or unsubstituted amine group, substituted or unsubstituted arylphosphino group, substituted or unsubstituted phosphinoxide group, substituted or unsubstituted Aryl group, or substituted or unsubstituted heteroaryl group.
Effects of the invention
The organic light emitting device of the present invention provides an organic light emitting device having a low driving voltage, high efficiency, and/or long life by including the compound represented by chemical formula 1 in the first organic layer, while including the compound represented by chemical formula 2 in the second organic layer.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, an electron-blocking layer 5, a light-emitting layer 6, a hole-blocking layer 7, and a cathode 9.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport and injection layer 8, and a cathode 9.
[ description of symbols ]
1: substrate
2: anode
3: hole injection layer
4: hole transport layer
5: electron blocking layer
6: luminescent layer
7: hole blocking layer
8: electron transport and injection layer
9: cathode electrode
Detailed Description
The present specification will be described in more detail below.
Provided is an organic light emitting device, including: a first electrode; a second electrode; a light-emitting layer provided between the first electrode and the second electrode; a first organic material layer provided between the first electrode and the light-emitting layer; and a second organic layer disposed between the second electrode and the light emitting layer, the first organic layer including a compound represented by chemical formula 1, and the second organic layer including a compound represented by chemical formula 2.
[ chemical formula 1]
In the above-described chemical formula 1,
ar1 and Ar2, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
r1 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or adjacent groups may be bonded to each other to form a ring,
n is an integer of 1 to 8, and when n is 2 or more, R1 may be the same or different from each other,
[ chemical formula 2]
In the above-described chemical formula 2,
l is a direct bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkoxy group having a valence of 2, a substituted or unsubstituted alkenyl group having a valence of 2, or a substituted or unsubstituted heteroarylene group,
ar3 and Ar4, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted arylalkyl, a substituted or unsubstituted arylalkenyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl,
x1 is N or CR11, X2 is N or CR12, X3 is N or CR13,
at least one of X1 to X3 is N,
r11 to R13 are the same as or different from each other, and each independently is hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester group, imide group, amide group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkylsulfonyl group, substituted or unsubstituted arylsulfonyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted silyl group, substituted or unsubstituted boron group, substituted or unsubstituted amine group, substituted or unsubstituted arylphosphine group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group.
In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.
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 other member but also a case where the other member exists between the two members.
In the context of the present specification,
indicates the position of the binding to the chemical formula or compound.
In the present specification, examples of the substituent are described below, but the substituent is not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group, a nitro group, an imide group, an amide group, a carbonyl group, an ether group, an ester group, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an alkenyl group, a silyl group, a boron group, an amine group, an arylphosphino group, a phosphinoxide group, an aryl group, and a heteroaryl group, or a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, a silyl group, an aryl group, and a heteroaryl group, or substituted with a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group, an alkyl group, a silyl group, an aryl group, and a heteroaryl group, or substituted with a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent.
Examples of the above-mentioned substituent are described below, but the substituent is not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the ester group may be — C (═ O) OR105or-OC (═ O) R106R is as defined above105And R106The same or different from each other, each independently is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group, but is not limited thereto. Specifically, the oxygen of the ester group may be substituted with an alkyl group having 1 to 25 carbon atoms, an alkenyl group having 1 to 25 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms. In one embodiment of the present specification, the oxygen is substituted with an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the amide group, the nitrogen of the amide group may be substituted with hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the silyl group may be represented by-SiYaYbYcThe above-mentioned chemical formula is Ya、YbAnd YcMay each be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. 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 represented BY-BYdYeThe above-mentioned chemical formula is YdAnd YeMay each be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. The boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.
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 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, and n-octyl.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 20. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, etc., but is not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30, 2 to 20, 2 to 10, or 2 to 5. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.
The alkyl group, the alkoxy group and other substituents containing an alkyl moiety described in the present specification are all included in a linear or branched form.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there are, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.
In the present specification, the amino group is-NH2The above-mentioned amino group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, a combination thereof, or the like. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms of the amine group is 1 to 20. According to one embodiment, the number of carbon atoms of the amine group is 1 to 10. Specific examples of the substituted amino group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, and a 9, 9-dimethylfluorenylbenzeneArylamine, pyridylphenylamine, diphenylamine, phenylpyridylamino, naphthylamine, biphenylamine, anthracenylamine, dibenzofuranylphenylamino, 9-methylanthrylamine, diphenylamine, phenylnaphthylamine, ditolylamino, phenyltolylamine, diphenylamine, etc., but not limited thereto.
In the present specification, the alkyl group in the alkylthio group and the alkylsulfonyl group is the same as exemplified above for the alkyl group. Specifically, examples of the alkylthio group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, and an octylthio group, and examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and a butylsulfonyl group, but the alkylthio group is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylene group, a triphenyl group, a perylene group,
Examples of the group include, but are not limited to, a fluorenyl group, a triphenylene group, and the like.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.
When the fluorenyl group is substituted, the compound may be
Isospirofluorene group;
(9, 9-dimethylfluorenyl group) and
and substituted fluorenyl groups such as (9, 9-diphenylfluorenyl) and the like. But is not limited thereto.
In the present specification, the aryl group in the aryloxy group can be applied to the description about the aryl group described above.
In the present specification, the aryl group in the arylthio group and the arylsulfonyl group is the same as the above-mentioned illustration of the aryl group.
In the present specification, the heterocyclic group is a cyclic group containing 1 or more of elements such as N, O, P, S, Si and Se as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuryl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuryl, benzonaphthothienyl, indenocarbazolyl, triazinyl and the like.
In the present specification, the heteroaryl group is an aromatic group, and the above description of the heterocyclic group can be applied thereto.
In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a hydrocarbon ring or a heterocyclic ring.
The hydrocarbon ring may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic, and may be selected from the cycloalkyl groups and the aryl groups described above, except for the 2-valent group.
In the present specification, the meaning that adjacent groups are bonded to each other to form a ring is that adjacent groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a fused ring thereof. The above-mentioned hydrocarbon ring means a ring composed of only carbon and hydrogen atoms. The heterocyclic ring is a ring containing 1 or more elements selected from N, O, P, S, Si and Se. In the present specification, the above-mentioned aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocyclic ring and aromatic heterocyclic ring may be monocyclic or polycyclic.
In the present specification, an aliphatic hydrocarbon ring means a ring which is not an aromatic ring and is composed of only carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1, 4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, but are not limited thereto.
In the present specification, the aromatic hydrocarbon ring refers to an aromatic ring composed of only carbon and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, perylene, and the like,
Pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, etc., but is not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as the aryl group.
In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing 1 or more heteroatoms. Examples of the aliphatic heterocyclic ring include ethylene oxide (oxirane), tetrahydrofuran, and 1, 4-bis
Examples of the alkyl group include, but are not limited to, alkyl (1,4-dioxane), pyrrolidine, piperidine, morpholine (morpholinone), oxepane, azocane, and thiacyclooctane.
In the present specification, an aromatic heterocyclic ring means an aromatic ring containing 1 or more heteroatoms. Examples of the aromatic heterocyclic ring include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, and the like,
Oxazole, iso
Oxazole, thiazole, isothiazole, triazole, and the like,
Diazoles, thiadiazoles, dithiazolesTetrazole, pyran, thiopyran, diazine,
Oxazine, thiazine, II
Alkene, triazine, tetrazine, isoquinoline, quinoline, benzoquinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazindene, indole, indolizine, benzothiazole, benzoquinone
Oxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, thiophene
Oxazines, indolocarbazoles, indenocarbazoles, and the like, but are not limited thereto.
The arylene group may have a valence of 2, and the description of the aryl group may be applied.
The above heteroaryl group can be used in addition to the 2-valent group.
Preferred embodiments of the present invention will be described in detail below. However, the embodiment of the present invention may be modified into various forms, and the scope of the present invention is not limited to the embodiment described below.
[ chemical formula 1]
In the above-described chemical formula 1,
ar1 and Ar2, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
r1 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or adjacent groups may be bonded to each other to form a ring,
n is an integer of 1 to 8, and when n is 2 or more, 2 or more R1 may be the same or different from each other.
According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms.
According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.
According to an embodiment of the present specification, Ar1 and Ar2, equal to or different from each other, are each independently an aryl group substituted or unsubstituted with an alkyl group or an aryl group.
According to an embodiment of the present specification, Ar1 and Ar2, equal to or different from each other, are each independently a monocyclic to tetracyclic aryl group substituted or unsubstituted with an alkyl group or a monocyclic to tetracyclic aryl group.
According to an embodiment of the present specification, Ar1 and Ar2, equal to or different from each other, are each independently a monocyclic to tricyclic aryl group substituted or unsubstituted with an alkyl group or a monocyclic to tricyclic aryl group.
According to an embodiment of the present specification, Ar1 and Ar2, equal to or different from each other, are each independently a monocyclic to bicyclic aryl group substituted or unsubstituted with an alkyl group or a monocyclic to bicyclic aryl group.
According to an embodiment of the present specification, Ar1 and Ar2, which are the same as or different from each other, are each independently an aryl group having 6 to 60 carbon atoms substituted with an alkyl group having 1 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms or unsubstituted.
According to an embodiment of the present specification, Ar1 and Ar2, which are the same as or different from each other, are each independently an aryl group of 6 to 30 carbon atoms substituted with an alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms or unsubstituted.
According to an embodiment of the present specification, Ar1 and Ar2, which are the same as or different from each other, are each independently an aryl group of 6 to 20 carbon atoms substituted with an alkyl group of 1 to 20 carbon atoms or an aryl group of 6 to 20 carbon atoms or unsubstituted.
According to an embodiment of the present specification, Ar1 and Ar2, which are the same as or different from each other, are each independently an aryl group of 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group of 1 to 10 carbon atoms or an aryl group of 6 to 14 carbon atoms.
According to an embodiment of the present specification, Ar1 and Ar2, which are the same or different from each other, are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted fluorenyl group.
According to an embodiment of the present specification, Ar1 and Ar2, which are the same or different from each other, are each independently a phenyl group substituted or unsubstituted with an alkyl group or an aryl group, a biphenyl group substituted or unsubstituted with an alkyl group or an aryl group, a naphthyl group substituted or unsubstituted with an alkyl group or an aryl group, a phenanthryl group substituted or unsubstituted with an alkyl group or an aryl group, a terphenyl group substituted or unsubstituted with an alkyl group or an aryl group, or a fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group.
According to an embodiment of the present specification, Ar1 and Ar2, which are the same or different from each other, are each independently a phenyl group substituted or unsubstituted with an aryl group, a biphenyl group substituted or unsubstituted with an aryl group, a naphthyl group substituted or unsubstituted with an aryl group, a phenanthryl group substituted or unsubstituted with an aryl group, a terphenyl group substituted or unsubstituted with an aryl group, or a fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group.
According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with an aryl group having 6 to 14 carbon atoms, a biphenyl group substituted or unsubstituted with an aryl group having 6 to 14 carbon atoms, a naphthyl group substituted or unsubstituted with an aryl group having 6 to 14 carbon atoms, a phenanthryl group substituted or unsubstituted with an aryl group having 6 to 14 carbon atoms, a terphenyl group substituted or unsubstituted with an aryl group having 6 to 14 carbon atoms, or a fluorenyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 14 carbon atoms.
According to an embodiment of the present specification, Ar1 and Ar2, equal to or different from each other, are each independently a phenyl group substituted or unsubstituted with a methyl group, a phenyl group, a naphthyl group or a phenanthryl group; biphenyl substituted or unsubstituted with methyl, phenyl, naphthyl or phenanthryl; naphthyl substituted or unsubstituted by methyl, phenyl, naphthyl or phenanthryl; phenanthryl substituted or unsubstituted with methyl, phenyl, naphthyl, or phenanthryl; terphenyl optionally substituted with methyl, phenyl, naphthyl or phenanthryl; or fluorenyl which is unsubstituted or substituted by methyl, phenyl, naphthyl or phenanthryl.
According to an embodiment of the present specification, Ar1 and Ar2, equal to or different from each other, are each independently a phenyl group substituted or unsubstituted with a phenyl group, a naphthyl group or a phenanthryl group; biphenyl substituted or unsubstituted with phenyl, naphthyl or phenanthryl; naphthyl substituted or unsubstituted by phenyl, naphthyl or phenanthryl; phenanthryl substituted or unsubstituted with phenyl, naphthyl or phenanthryl; terphenyl optionally substituted with phenyl, naphthyl or phenanthryl; or fluorenyl substituted or unsubstituted by methyl.
According to an embodiment of the present specification, Ar1 and Ar2, equal to or different from each other, are each independently a phenyl group substituted or unsubstituted with a phenyl group, a naphthyl group or a phenanthryl group; a biphenyl group; a naphthyl group; phenanthryl; a terphenyl group; or fluorenyl substituted or unsubstituted by methyl.
According to an embodiment of the present specification, Ar1 and Ar2, equal to or different from each other, are each independently a phenyl group substituted or unsubstituted with a phenyl group, a naphthyl group or a phenanthryl group; a biphenyl group; phenanthryl; a terphenyl group; or a dimethylfluorenyl group.
According to an embodiment of the present specification, Ar1 and Ar2, equal to or different from each other, are each independently a phenyl group substituted or unsubstituted with a phenyl group, a naphthyl group or a phenanthryl group; a biphenyl group; a terphenyl group; or a dimethylfluorenyl group.
According to an embodiment of the present specification, Ar1 and Ar2, equal to or different from each other, are each independently a phenyl group substituted or unsubstituted with a phenyl group, a naphthyl group or a phenanthryl group; a biphenyl group; or a terphenyl group.
According to an embodiment of the present specification, Ar1 and Ar2, equal to or different from each other, are each independently phenyl substituted or unsubstituted with phenyl or naphthyl; a biphenyl group; or a terphenyl group.
According to an embodiment of the present specification, Ar1 and Ar2, which are the same or different from each other, may each be independently selected from the following structures.
In the above structure, the dotted line indicates the bonding position.
In the above structure, R6 is alkyl or aryl.
In the above structure, R6 is an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
In the above structure, R6 is an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
In the above structure, R6 is methyl or phenyl.
In the above structure, R6 is methyl.
In the above structure, R7 is a substituted or unsubstituted aryl group.
In the above structure, R7 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.
According to an embodiment of the present specification, Ar1 and Ar2, which are the same or different from each other, may each be independently selected from the following structures.
In the above structure, the dotted line indicates the bonding position.
According to one embodiment of the present description, Ar1 is represented by-L101-Ar 101 and Ar2 is represented by-L102-Ar 102.
According to an embodiment of the present specification, L101 and L102, which are the same or different from each other, are each independently a direct bond, or a substituted or unsubstituted arylene group.
According to an embodiment of the present description, L101 and L102, equal to or different from each other, are each independently a direct bond, or an arylene group.
According to an embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently is a direct bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
According to an embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
According to an embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently is a direct bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
According to an embodiment of the present specification, L101 and L102, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
According to an embodiment of the present specification, L101 and L102 are the same as or different from each other, and each is independently a direct bond, a phenylene group, or a biphenylene group.
According to an embodiment of the present specification, L101 and L102, which are the same or different from each other, are each independently a direct bond, or a phenylene group.
According to an embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group.
According to an embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently is an aryl group substituted or unsubstituted with an alkyl group or an aryl group.
According to an embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently is an aryl group of 6 to 60 carbon atoms substituted or unsubstituted with an alkyl group of 1 to 60 carbon atoms or an aryl group of 6 to 60 carbon atoms.
According to an embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently is an aryl group of 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms.
According to an embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently is an aryl group of 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group of 1 to 20 carbon atoms or an aryl group of 6 to 20 carbon atoms.
According to an embodiment of the present specification, Ar101 and Ar102, which are the same or different from each other, are each independently a monocyclic to tetracyclic aryl group substituted or unsubstituted with an alkyl group or a monocyclic to tetracyclic aryl group.
According to an embodiment of the present specification, Ar101 and Ar102, which are the same or different from each other, are each independently a monocyclic to tricyclic aryl group substituted or unsubstituted with an alkyl group or a monocyclic to tricyclic aryl group.
According to an embodiment of the present specification, Ar101 and Ar102, which are the same or different from each other, are each independently a monocyclic to bicyclic aryl group substituted or unsubstituted with an alkyl group or a monocyclic to bicyclic aryl group.
According to an embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted fluorenyl group.
According to an embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently is a phenyl group substituted or unsubstituted with an alkyl group or an aryl group, a biphenyl group substituted or unsubstituted with an alkyl group or an aryl group, a naphthyl group substituted or unsubstituted with an alkyl group or an aryl group, a phenanthryl group substituted or unsubstituted with an alkyl group or an aryl group, a terphenyl group substituted or unsubstituted with an alkyl group or an aryl group, or a fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group.
According to an embodiment of the present specification, Ar101 and Ar102, which are the same or different from each other, are each independently a phenyl group substituted or unsubstituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthryl group; biphenyl substituted or unsubstituted with methyl, phenyl, naphthyl or phenanthryl; naphthyl substituted or unsubstituted by methyl, phenyl, naphthyl or phenanthryl; phenanthryl substituted or unsubstituted with methyl, phenyl, naphthyl, or phenanthryl; terphenyl optionally substituted with methyl, phenyl, naphthyl or phenanthryl; or fluorenyl which is unsubstituted or substituted by methyl, phenyl, naphthyl or phenanthryl.
According to an embodiment of the present specification, Ar101 and Ar102, which are the same or different from each other, are each independently a phenyl group substituted or unsubstituted with a phenyl group, a naphthyl group or a phenanthryl group; biphenyl substituted or unsubstituted with phenyl, naphthyl or phenanthryl; naphthyl substituted or unsubstituted by phenyl, naphthyl or phenanthryl; phenanthryl substituted or unsubstituted with phenyl, naphthyl or phenanthryl; terphenyl optionally substituted with phenyl, naphthyl or phenanthryl; or fluorenyl substituted or unsubstituted by methyl.
According to an embodiment of the present specification, Ar101 and Ar102, which are the same or different from each other, are each independently a phenyl group substituted or unsubstituted with a phenyl group, a naphthyl group or a phenanthryl group; a biphenyl group; a naphthyl group; phenanthryl; a terphenyl group; or fluorenyl substituted or unsubstituted by methyl.
According to an embodiment of the present specification, Ar101 and Ar102, which are the same or different from each other, are each independently a phenyl group substituted or unsubstituted with a phenyl group, a naphthyl group or a phenanthryl group; a biphenyl group; a naphthyl group; phenanthryl; a terphenyl group; or a dimethylfluorenyl group.
According to an embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, or a fluorenyl group substituted or unsubstituted with a methyl group.
According to an embodiment of the present specification, Ar101 and Ar102, equal to or different from each other, are each independently a phenyl group; a biphenyl group; terphenyl or naphthyl.
According to an embodiment of the present specification, R1 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.
According to one embodiment of the present specification, R1 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.
According to one embodiment of the present specification, R1 is hydrogen or deuterium, or bonds with adjacent groups to form an aromatic hydrocarbon ring fused to a carbazole.
According to one embodiment of the present specification, R1 is hydrogen or is bonded to an adjacent group to form an aromatic hydrocarbon ring fused to carbazole.
According to an embodiment of the present specification, R1 is hydrogen, or combines with adjacent groups to form a benzene ring fused to carbazole.
According to one embodiment of the present description, R1 is hydrogen.
According to an embodiment of the present specification, R1 and an adjacent group are bonded to each other to form a benzene ring fused on carbazole.
According to an embodiment of the present specification, when n is an integer of 1 to 8 and n is 2 or more, 2 or more R1 are the same or different from each other.
According to one embodiment of the present specification, n is 1.
According to an embodiment of the present specification, n is 2.
According to an embodiment of the present description, n is 8.
According to one embodiment of the present specification, in the case where N of carbazole is connected to ortho (ortho) position or meta (meta) position of biphenylene group connected to amine group in the chemical formula 1, voltage, efficiency, and lifetime characteristics are further increased.
According to an embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 1-1 or 1-2.
[ chemical formula 1-1]
[ chemical formulas 1-2]
In the above chemical formulas 1-1 and 1-2, Ar1, Ar2, R1 and n are defined as in the above chemical formula 1.
According to an embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-3 to 1-6.
[ chemical formulas 1-3]
[ chemical formulas 1 to 4]
[ chemical formulas 1 to 5]
[ chemical formulas 1 to 6]
In the above chemical formulas 1-3 to 1-6, Ar1 and Ar2 are defined as in the above chemical formula 1,
g1 and G2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
g1 is an integer from 1 to 10,
g2 is an integer from 1 to 8,
when G1 is 2 or more, 2 or more G1 s are the same or different from each other, and when G2 is 2 or more, 2 or more G2 s are the same or different from each other.
According to an embodiment of the present description, G1 and G2 are the same or different from each other and are hydrogen or deuterium.
According to an embodiment of the present description, G1 and G2 are hydrogen.
According to an embodiment of the present description, g1 is 1.
According to an embodiment of the present description, g1 is 10.
According to an embodiment of the present description, g2 is 1.
According to an embodiment of the present description, g2 is 8.
According to one embodiment of the present specification, the compound represented by the above chemical formula 1 is represented by any one of the following structural formulae.
[ chemical formula 2]
In the above-described chemical formula 2,
l is a direct bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkoxy group having a valence of 2, a substituted or unsubstituted alkenyl group having a valence of 2, or a substituted or unsubstituted heteroarylene group,
ar3 and Ar4, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted arylalkyl, a substituted or unsubstituted arylalkenyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl,
x1 is N or CR11, X2 is N or CR12, X3 is N or CR13,
at least one of X1 to X3 is N,
r11 to R13 are the same as or different from each other, and each independently is hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester group, imide group, amide group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkylsulfonyl group, substituted or unsubstituted arylsulfonyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted silyl group, substituted or unsubstituted boron group, substituted or unsubstituted amine group, substituted or unsubstituted arylphosphine group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group.
According to an embodiment of the present specification, L is a direct bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkoxy group having a valence of 2, a substituted or unsubstituted alkenyl group having a valence of 2, or a substituted or unsubstituted heteroarylene group.
According to an embodiment of the present description, L is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.
According to an embodiment of the present description, L is a direct bond, or a substituted or unsubstituted arylene.
According to an embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
According to an embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
According to an embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
According to an embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
According to an embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
According to an embodiment of the present specification, L is a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
According to an embodiment of the present description, L is a direct bond, phenylene or biphenylene.
According to an embodiment of the present specification, L is a direct bond, or a phenylene group.
According to an embodiment of the present specification, L is a direct bond, or may be any one selected from the following structural formulae.
In the above structure, the dotted line indicates the bonding position.
In the above structure, R101 to R103 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
According to an embodiment of the present specification, R101 to R103, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
According to an embodiment of the present specification, R101 to R103 are the same or different from each other, and each is independently a methyl group or a phenyl group.
According to an embodiment of the present specification, R101 and R102, which are the same or different from each other, are each independently a methyl group or a phenyl group.
According to an embodiment of the present description, R103 is phenyl.
According to an embodiment of the present specification, L is a direct bond, or may be any one selected from the following structural formulae.
In the above structural formulae, the dotted line represents a binding site.
According to an embodiment of the present specification, Ar3 and Ar4, equal to or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted arylalkyl, a substituted or unsubstituted arylalkenyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl.
According to an embodiment of the present specification, Ar3 and Ar4, equal to or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present specification, Ar3 and Ar4, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
According to an embodiment of the present specification, Ar3 and Ar4, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present specification, Ar3 and Ar4, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
According to an embodiment of the present specification, Ar3 and Ar4, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms.
According to an embodiment of the present specification, Ar3 and Ar4, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 10 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.
According to an embodiment of the present specification, Ar3 and Ar4, equal to or different from each other, are each independently a substituted or unsubstituted monocyclic to hexacyclic aryl group or a substituted or unsubstituted monocyclic to hexacyclic heteroaryl group.
According to an embodiment of the present specification, Ar3 and Ar4, equal to or different from each other, are each independently a substituted or unsubstituted monocyclic to pentacyclic aryl group or a substituted or unsubstituted monocyclic to pentacyclic heteroaryl group.
According to an embodiment of the present specification, Ar3 and Ar4, equal to or different from each other, are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group, or a substituted or unsubstituted monocyclic to tetracyclic heteroaryl group.
According to an embodiment of the present specification, Ar3 and Ar4, equal to or different from each other, are each independently a substituted or unsubstituted monocyclic to tricyclic aryl group, or a substituted or unsubstituted monocyclic to tricyclic heteroaryl group.
According to an embodiment of the present specification, Ar3 and Ar4, which are the same as or different from each other, are each independently an aryl group substituted or unsubstituted with 1 or more groups selected from deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, and an aryl group, or 2 or more groups linked among the above-mentioned substituents; or a heteroaryl group which is unsubstituted or substituted with 1 or more groups selected from deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or 2 or more groups bonded to the above-mentioned substituents.
According to an embodiment of the present specification, Ar3 and Ar4, equal to or different from each other, are each independently an aryl group substituted or unsubstituted with deuterium, a halogen group, a cyano group, an alkylsilyl group, an alkyl group, or an aryl group; or heteroaryl substituted or unsubstituted with deuterium, a halogen group, cyano, alkylsilyl, alkyl or aryl.
According to an embodiment of the present specification, Ar3 and Ar4, which are the same or different from each other, are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
According to an embodiment of the present specification, Ar3 and Ar4, which are the same or different from each other, are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a fluorenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, which may be substituted or unsubstituted with 1 or more groups selected from deuterium, a halogen group, a cyano group, an alkylsilyl group, an alkyl group, and an aryl group.
According to an embodiment of the present specification, Ar3 and Ar4, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted with 1 or more groups selected from deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, and an aryl group, or 2 or more groups linked among the above-mentioned substituents; biphenyl substituted or unsubstituted with 1 or more groups selected from deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or 2 or more groups linked to the above-mentioned substituent; a terphenyl group which is substituted or unsubstituted with 1 or more groups selected from deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or 2 or more groups bonded to the above-mentioned substituents; naphthyl substituted or unsubstituted with 1 or more groups selected from deuterium, a halogen group, cyano, silyl, alkyl, and aryl, or 2 or more groups linked to the above-mentioned substituent; phenanthryl substituted or unsubstituted with 1 or more groups selected from deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, and an aryl group, or 2 or more groups linked to the above-mentioned substituent; a triphenylene group which is substituted or unsubstituted with 1 or more groups selected from deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or 2 or more groups bonded to the above-mentioned substituent; a fluorenyl group which is substituted or unsubstituted with 1 or more groups selected from deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group or 2 or more groups linked to the above-mentioned substituent; dibenzofuranyl substituted or unsubstituted with 1 or more groups selected from deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, and an aryl group, or 2 or more groups bonded to the above-mentioned substituents; or a dibenzothienyl group which is substituted or unsubstituted by 1 or more groups selected from deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or by 2 or more groups bonded to the above-mentioned substituents.
According to an embodiment of the present specification, Ar3 and Ar4, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted with 1 or more groups selected from deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, and an aryl group, or 2 or more groups linked among the above-mentioned substituents; biphenyl substituted or unsubstituted with deuterium or cyano; a terphenyl group; naphthyl substituted or unsubstituted with aryl; phenanthryl; a triphenylene group; fluorenyl substituted or unsubstituted with alkyl or aryl; a dibenzofuranyl group; or a dibenzothienyl group.
According to an embodiment of the present specification, Ar3 and Ar4, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted with 1 or more groups selected from deuterium, fluoro (-F), cyano, silyl, methyl, tert-butyl, phenyl, naphthyl, and phenanthryl, or 2 or more groups linked among the above-mentioned substituents; biphenyl substituted or unsubstituted with cyano; a terphenyl group; naphthyl substituted or unsubstituted by phenyl; phenanthryl; a triphenylene group; fluorenyl substituted or unsubstituted with methyl; a dibenzofuranyl group; or a dibenzothienyl group.
According to an embodiment of the present specification, Ar3 and Ar4, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted with deuterium, fluoro (-F), cyano, trimethylsilyl, tert-butyl, phenyl, naphthyl, and phenanthryl; biphenyl substituted or unsubstituted with deuterium, fluoro (-F), cyano, trimethylsilyl, tert-butyl, phenyl, naphthyl, and phenanthryl; terphenyl optionally substituted with deuterium, fluoro (-F), cyano, trimethylsilyl, tert-butyl, phenyl, naphthyl and phenanthryl; naphthyl substituted or unsubstituted with deuterium, fluoro (-F), cyano, trimethylsilyl, tert-butyl, phenyl, naphthyl and phenanthryl; phenanthryl substituted or unsubstituted with deuterium, fluoro (-F), cyano, trimethylsilyl, tert-butyl, phenyl, naphthyl, and phenanthryl; triphenylene substituted or unsubstituted with deuterium, fluoro (-F), cyano, trimethylsilyl, tert-butyl, phenyl, naphthyl, and phenanthryl; fluorenyl substituted or unsubstituted with deuterium, fluoro (-F), cyano, trimethylsilyl, t-butyl, phenyl, naphthyl, and phenanthryl; dibenzofuranyl substituted or unsubstituted with deuterium, fluoro (-F), cyano, trimethylsilyl, tert-butyl, phenyl, naphthyl and phenanthryl; or a dibenzothienyl group which is unsubstituted or substituted by deuterium, a fluoro group (-F), a cyano group (-CN), a trimethylsilyl group (-trimethylsilyl), a tert-butyl group (-TBL), a phenyl group (-naphthyl), a naphthyl group and a phenanthryl group (-phenanthryl).
According to an embodiment of the present specification, Ar3 and Ar4, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted with deuterium, fluoro (-F), cyano, trimethylsilyl, tert-butyl, phenyl, naphthyl, or phenanthryl; biphenyl substituted or unsubstituted with deuterium, fluoro (-F), cyano, trimethylsilyl, tert-butyl, phenyl, naphthyl or phenanthryl; terphenyl optionally substituted with deuterium, fluoro (-F), cyano, trimethylsilyl, tert-butyl, phenyl, naphthyl or phenanthryl; naphthyl substituted or unsubstituted by phenyl, naphthyl or phenanthryl; phenanthryl substituted or unsubstituted with phenyl, naphthyl or phenanthryl; a triphenylene group substituted or unsubstituted with a phenyl group, a naphthyl group or a phenanthryl group; a dimethyl fluorenyl group; a dibenzofuranyl group; or a dibenzothienyl group.
According to an embodiment of the present specification, Ar3 and Ar4, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted with deuterium, fluoro (-F), cyano, trimethylsilyl, tert-butyl, phenyl, naphthyl, or phenanthryl; biphenyl substituted or unsubstituted with cyano; a terphenyl group; naphthyl substituted or unsubstituted by phenyl; phenanthryl; a triphenylene group; a dimethyl fluorenyl group; a dibenzofuranyl group; or a dibenzothienyl group.
According to an embodiment of the present specification, Ar3 and Ar4, equal to or different from each other, are each independently phenyl substituted with naphthyl or unsubstituted; a biphenyl group; or a terphenyl group.
According to an embodiment of the present specification, Ar3 and Ar4, equal to or different from each other, are each independently phenyl substituted with naphthyl or unsubstituted; or a terphenyl group.
According to an embodiment of the present disclosure, Ar3 and Ar4 may be the same or different from each other, and may be each independently selected from the following structures.
The above structure is substituted or unsubstituted with deuterium, a halogen group, cyano, alkylsilyl or alkyl, and the dotted line indicates the bonding position.
The above structure is substituted or unsubstituted with deuterium, fluoro (-F), cyano, trimethylsilyl or tert-butyl.
In the above structure, R6 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
In the above structure, R6 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In the above structure, R6 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In the above structure, R6 is methyl or phenyl.
In the above structure, R7 is a substituted or unsubstituted aryl group.
In the above structure, R7 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In the above structure, R7 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In the above structure, R7 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.
In the above structure, R7 is phenyl or naphthyl.
According to an embodiment of the present disclosure, Ar3 and Ar4 may be the same or different from each other, and may be each independently selected from the following structures.
The above structure is substituted or unsubstituted with deuterium, a halogen group, cyano, alkylsilyl or alkyl, the dotted line represents the binding site, and R6 is as defined above.
According to an embodiment of the present specification, any one of Ar3 and Ar4 described above is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present disclosure, Ar3 and Ar4 are substituted or unsubstituted aryl groups and are different from each other.
According to an embodiment of the present disclosure, X1 is N or CR11, X2 is N or CR12, X3 is N or CR13, and at least one of X1 to X3 is N.
According to an embodiment of the present description, at least one of X1 to X3 is N.
According to an embodiment of the present description, at least 2 of X1 to X3 are N.
According to an embodiment of the present description, X1, X2, and X3 are N.
According to an embodiment of the present description, X1 and X2 are N and X3 is CR 13.
According to an embodiment of the present description, X1 and X3 are N and X2 is CR 12.
According to an embodiment of the present description, X2 and X3 are N and X1 is CR 11.
According to an embodiment of the present disclosure, X1 is N, X2 is CR12, and X3 is CR 13.
According to an embodiment of the present disclosure, X2 is N, X1 is CR11, and X3 is CR 13.
According to an embodiment of the present disclosure, X3 is N, X1 is CR11, and X2 is CR 12.
According to an embodiment of the present description, R11 to R13, equal to or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present specification, R11 to R13, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present specification, R11 to R13, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
According to an embodiment of the present description, R11 to R13 are hydrogen or deuterium.
According to an embodiment of the present description, R11 to R13 are hydrogen.
According to an embodiment of the present specification, the chemical formula 2 is represented by any one of the following chemical formulas 2-1 to 2-4.
[ chemical formula 2-1]
[ chemical formula 2-2]
[ chemical formulas 2-3]
[ chemical formulas 2-4]
In the above chemical formulas 2-1 to 2-4, L, Ar3, Ar4, and X1 to X3 are defined as in the above chemical formula 2.
According to an embodiment of the present specification, the compound represented by the above chemical formula 2 is represented by any one of the following structural formulae.
In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In the present invention, the HOMO and LUMO levels of the compounds can also be adjusted by introducing various substituents into the core structure of the above-described structure.
The organic light emitting device of the present invention may be manufactured using a general method and material for manufacturing an organic light emitting device, in addition to forming a first organic layer between the first electrode and the light emitting layer using the compound of chemical formula 1 and forming a second organic layer between the second electrode and the light emitting layer using the compound of chemical formula 2.
The organic layer can be formed by using the above compound not only by a vacuum evaporation method but also by a solution coating method in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including 1 or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number or a larger number of organic layers may be included.
The organic light emitting device of the present invention includes a light emitting layer, a first organic layer disposed between a first electrode and the light emitting layer includes a compound represented by chemical formula 1, and a second organic layer disposed between a second electrode and the light emitting layer includes a compound represented by chemical formula 2.
According to one example, the organic layer including the compound of the above chemical formula 1 has a thickness of
To
Preferably, it is
To
According to one example, the organic layer including the compound of the above chemical formula 2 has a thickness of
To
Preferably, it is
To
According to one example, the first organic layer disposed between the first electrode and the emission layer of the organic light emitting device of the present invention includes a hole injection layer, a hole transport layer, or a hole injection and transport layer including the compound represented by the above chemical formula 1.
According to one example, the first organic layer disposed between the first electrode and the emission layer of the organic light emitting device of the present invention may be a hole injection layer, a hole transport layer, or a hole injection and transport layer, which may include the compound represented by the above chemical formula 1.
According to one example, the first organic layer disposed between the first electrode and the emission layer of the organic light emitting device of the present invention includes an electron blocking layer including the compound represented by the above chemical formula 1.
According to one example, the first organic layer disposed between the first electrode and the light emitting layer of the organic light emitting device of the present invention is an electron blocking layer, and the electron blocking layer may include the compound represented by the above chemical formula 1.
According to one example, the second organic layer disposed between the second electrode and the emission layer of the organic light emitting device of the present invention includes an electron injection layer, an electron transport layer, or an electron injection and transport layer including the compound represented by the above chemical formula 1.
According to one example, the second organic layer disposed between the second electrode and the emission layer of the organic light emitting device of the present invention may be an electron injection layer, an electron transport layer, or an electron injection and transport layer, which may include the compound represented by the above chemical formula 1.
According to one example, the second organic layer disposed between the second electrode and the emission layer of the organic light emitting device of the present invention includes a hole blocking layer including the compound represented by the above chemical formula 2.
According to one example, the second organic layer disposed between the second electrode and the emission layer of the organic light emitting device of the present invention is a hole blocking layer, and the hole blocking layer may include the compound represented by the above chemical formula 2.
In another embodiment, the first organic layer may include other organic compounds, metals, or metal compounds in addition to the compound represented by chemical formula 1.
In another embodiment, the second organic layer may include other organic compounds, metals, or metal compounds in addition to the compound represented by chemical formula 2.
The organic light emitting device of the present invention may further include one or more organic layers of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.
According to one example, the first organic layer is in contact with the light-emitting layer. Here, the contact means that no other organic layer is present between the light-emitting layer and the first organic layer.
According to one example, the second organic layer is in contact with the light-emitting layer. Here, the contact means that no other organic layer is present between the light-emitting layer and the second organic layer.
In the organic light emitting device of the present invention, the organic layer may include an electron blocking layer, and the electron blocking layer may use a material known in the art.
According to one example, the second organic layer is in contact with the hole blocking layer. Here, the contact means that no other organic layer is present between the hole blocking layer and the second organic layer.
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.
For example, the organic light emitting device may have a stacked structure as shown below, but is not limited thereto.
(1) Anode/hole transport layer/light emitting layer/cathode
(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode
(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(5) Anode/hole transport layer/luminescent layer/electron transport layer/electron injection layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode
(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(10) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(11) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(12) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(13) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(14) Anode/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/cathode
(15) Anode/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(17) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(18) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer
(19) Anode/hole injection layer/first hole transport layer/second hole transport layer/luminescent layer/hole blocking layer/electron transport layer/electron injection layer/cathode/cladding layer
(20) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport and injection layer/cathode
The structure of the organic light emitting device of the present invention may have the structure shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, and a cathode 9 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2 may be contained in the above electron blocking layer 5, the light emitting layer 6, or the hole blocking layer 7.
Fig. 2 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport and injection layer 8, and a cathode 9 are sequentially stacked. In the structure as described above, the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2 may be contained in the above hole injection layer 3, hole transport layer 4, electron blocking layer 5, light emitting layer 6, hole blocking layer 7, or electron transport and injection layer 8.
For example, the organic light emitting device according to the present invention may be manufactured as follows: the organic el device is manufactured by forming an anode by evaporating metal or a metal oxide having conductivity or an alloy thereof on a substrate by a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer on the anode, and then evaporating a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
The organic layer may further include 1 or more layers of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.
The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting electrons, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, and the like, but is not limited thereto and may have a single-layer structure. The organic layer can be produced as a smaller number of layers by a solvent process (solvent process) other than the vapor deposition method, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method, using various polymer materials.
The anode is an electrode for injecting holes, and a substance having a large work function is generally preferable as an anode substance so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, 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.
The cathode is an electrode for injecting electrons, and a substance having a small work function is generally preferable as a cathode substance in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection layer is a layer that functions to smoothly inject holes from the anode into the light-emitting layer, and the hole injection substance is a substance that can inject holes from the anode well at a low voltage, and preferably, the HOMO (highest occupied molecular orbital) of the hole injection substance is interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrine), 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 thickness of the hole injection layer may be 1 to 150 nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the hole injection property can be prevented from being lowered, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the driving voltage can be prevented from being increased to increase the movement of holes when the thickness of the hole injection layer is too large.
The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
A hole buffer layer may be further disposed between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
An electron blocking layer may be disposed between the hole transport layer and the light emitting layer. In the above electron blocking layer, the above-mentioned compound or a material known in the art may be used.
The light-emitting layer may emit red, green or blue light, and may be formed of a phosphorescent substance or a fluorescent substance. The light-emitting substance 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 high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is 8-hydroxy-quinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
As a host material of the light-emitting layer, there are aromatic fused ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the aromatic fused ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder furan compound, a pyrimidine derivative, and the like, but is not limited thereto.
When the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent material such as piqir (acac) (bis (1-phenylisoquinoline) acetylacetonatoiridium, bis (1-phenylisoquinoline) acetylacetonatoiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonatoiridium, bis (1-phenylquinoline) acetylacetonatoiridium), PQIr (tris (1-phenylquinoline) iridium, tris (1-phenylquinoline) iridium), PtOEP (octylporphyrin, platinum octaethylporphyrin), or Alq (r) may be used3(tris (8-hydroxyquinolino) aluminum), etc., but is not limited thereto. When the light-emitting layer emits green light, Ir (ppy) can be used as a light-emitting dopant3Phosphorescent substances such as fac tris (2-phenylpyridine) iridium, and Alq tris (2-phenylpyridine) iridium3(tris (8-hydroxyquinolino) aluminum), etc., but is not limited thereto. When the light-emitting layer emits blue light, (4, 6-F) may be used as the light-emitting dopant2ppy)2Examples of the fluorescent substance include phosphorescent substances such as Irpic and fluorescent substances such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), Distyrylbenzene (DSB), Distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers, but the fluorescent substances are not limited thereto.
A hole blocking layer may be disposed between the electron transport layer and the light emitting layer, and materials known in the art may be used.
The electron transport layer can play a role in smoothly transporting electrons. The electron transport material is a material that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and is preferably a material having a high mobility to electrons. As specific examples, there are the above-mentioned compounds or Al complexes of 8-hydroxyquinoline, Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. Electronic transmitterThe thickness of the input layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the electron transport property can be prevented from being lowered, and when the thickness of the electron transport layer is 50nm or less, there is an advantage that the driving voltage can be prevented from being increased to increase the movement of electrons when the thickness of the electron transport layer is too large.
The electron injection layer can perform a function of smoothly injecting electrons. As the electron-injecting substance, the following compounds are preferred: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and having an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The 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 injection layer. Specifically, there are
Oxadiazole or triazole derivatives, phenanthroline derivativesExamples of the metal compound include, but are not limited to, BCP, aluminum complex, and the like.
The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
Modes for carrying out the invention
Hereinafter, in order to specifically explain the present specification, the detailed description will be given by referring to examples. However, the embodiments described in the present specification may be modified into various forms, and the scope of the present application is not to be construed as being limited to the embodiments described in detail below. The embodiments of the present application are provided to more fully explain the present specification to those skilled in the art.
Production examples a to C: production of intermediates A to C
Intermediates a to C were produced by the procedure described above.
Production example 1: production of Compound 1-1
In a 500ml round-bottomed flask under nitrogen atmosphere, the compound N- (4-bromophenyl) -N- (4- (naphthalen-1-yl) phenyl) - [1,1':4',1 '-terphenyl ] -4-amine (N- (4-bromophenyl) -N- (4- (naphthalene N-1-yl) phenyl) - [1,1':4', 1' -terphenyl ] -4-amine) (12.32g, 20.50mmol), 2- (9H-carbazol-9-yl) phenyl) boronic acid ((2- (9H-carbazol-9-yl) phenyl) boronic acid) (6.47g, 22.55mmol) was completely dissolved in 240ml of tetrahydrofuran, 2M aqueous potassium carbonate (120ml) was added, tetrakis (triphenylphosphine) palladium (0.42g was added, 0.37mmol), the mixture was stirred with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 350ml of ethyl acetate to obtain compound 1-1(11.29g, 72%).
MS[M+H]+＝765
Production example 2: production of Compound 1-2
In a 500ml round bottom flask under nitrogen, the compound 4-bromo-N, N-bis (4- (naphthalen-2-yl) phenyl) aniline (4-bromo-N, N-bis (4- (naphthalen-2-yl) phenyl) aniline) (11.09g, 19.25mmol) and (2- (9H-carbazol-9-yl) phenyl) boronic acid (6.08g, 21.18mmol) were completely dissolved in 240ml tetrahydrofuran, 2M aqueous potassium carbonate (120ml) was added, tetrakis (triphenylphosphine) palladium (0.67g, 0.58mmol) was added, and stirring was carried out for 3 hours under heating. The temperature was lowered to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250ml of ethyl acetate to obtain compound 1-2(8.88g, 62%).
MS[M+H]+＝739
Production example 3: production of Compounds 1 to 3
In a 500ml round-bottom flask, the compound N- ([1,1'-biphenyl ] -4-yl) -N- (4-bromophenyl) - [1,1':3',1 "-terphenyl ] -4' -amine (N- ([1,1'-biphenyl ] -4-yl) -N- (4-bromophenyl) - [1,1':3', 1" -terphenyl ] -4' -amine) (10.55g, 19.11mmol), (2- (9H-carbazol-9-yl) phenyl) boronic acid (6.03g, 21.02mmol) was completely dissolved in 240ml of tetrahydrofuran, 2M aqueous potassium carbonate (120ml) was added, and after adding tetrakis (triphenylphosphine) palladium (0.66g, 0.57mmol), the mixture was stirred under heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 280ml of ethyl acetate to obtain compound 1-3(9.07g, 66%).
MS[M+H]+＝715
Production example 4: production of Compound 2-1
In a 500ml round-bottomed flask, under nitrogen, Compound A (11.71g, 25.56mmol), 2- ([1,1':2',1 "-terphenyl ] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (2- ([1,1':2', 1" -terphenyl ] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine) (9.76, 23.24mmol) were completely dissolved in 240ml of tetrahydrofuran, 2M aqueous potassium carbonate (120ml) was added, and after addition of tetrakis (triphenylphosphine) palladium (0.81g, 0.70mmol), stirring was carried out with heating for 7 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration under reduced pressure was performed, followed by recrystallization from 260ml of tetrahydrofuran, thereby producing compound 2-1(10.02g, 60%).
MS[M+H]+＝716
Production example 5: production of Compound 2-2
Compound B (10.95g, 23.90mmol), 2-chloro-4- (3- (naphthalen-1-yl) phenyl) -6-phenyl-1,3,5-triazine (2-chloro-4- (3- (naphthalen-1-yl) phenyl) -6-phenyl-1,3,5-triazine) (8.56, 21.73mmol) was completely dissolved in 280ml of tetrahydrofuran under a nitrogen atmosphere in a 500ml round-bottom flask, 2M aqueous potassium carbonate (140ml) was added, and tetrakis (triphenylphosphine) palladium (0.81g, 0.70mmol) was added, followed by stirring with heating for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 290ml of acetonitrile, thereby producing compound 2-2(7.96g, 53%).
MS[M+H]+＝690
Production example 6: production of Compound 2-3
Compound C (12.26g, 26.76mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine) (9.44g, 24.33mmol) were completely dissolved in 260ml of tetrahydrofuran under a nitrogen atmosphere in a 500ml round-bottomed flask, and 2M aqueous potassium carbonate (130ml) was added, followed by addition of tetrakis (triphenylphosphine) palladium (0.84g, 0.73mmol) and stirring with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration under reduced pressure was performed, followed by recrystallization from 260ml of tetrahydrofuran, thereby producing compound 2-3(8.36g, 54%).
MS[M+H]+＝640
Comparative example 1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone and methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, the following chemical formula [ HI-1 ] was added]And the following chemical formula [ HI-2]So as to be in a ratio of 98:2 (molar ratio) to
The hole injection layer is formed by thermal vacuum deposition.
On the hole injection layer, the following compound [ HT-1 ] as a hole-transporting substance was added]
Vacuum evaporation is performed to form a hole transport layer.
Then, on the hole transport layer, the film thickness
The following compound [ EB-1]]
Vacuum evaporation is performed to form an electron blocking layer.
Then, on the electron blocking layer, the film thickness
Will be shown below as [ BH-1]And [ BD-1]The light-emitting layer was formed by vacuum evaporation at a weight ratio of 40: 1.
On the light-emitting layer, the thickness of the film
The above compound [ HB-1]]The hole blocking layer is formed by vacuum evaporation.
Next, on the hole-blocking layer, a compound [ ET-1 ]]And the above compound LiQ (Lithium Quinolate) was vacuum-evaporated at a weight ratio of 1:1 to obtain a solution
The thickness of (a) forms an electron injection and transport layer.
On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
the thickness of (3) is evaporated to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vapor deposition rate of (2) is maintained at a vacuum degree of 2X 10 during vapor deposition-7～5×10-6And supporting to thereby fabricate an organic light emitting device.
Experimental examples 1-1 to 1-9
An organic light-emitting device was produced in the same manner as in comparative example 1, except that the compounds described in Table 1 below were used in place of the compounds [ EB-1] and [ HB-1] of comparative example 1.
Comparative examples 2 to 14
An organic light-emitting device was produced in the same manner as in comparative example 1, except that the compounds described in Table 1 below were used in place of the compounds [ EB-1] and [ HB-1] of comparative example 1.
The organic light emitting devices manufactured in the above experimental examples and comparative examples were applied with 10mA/cm2At a current of 10mA/cm, the driving voltage, the luminous efficiency and the color coordinate were measured2The time until the initial luminance reached 95% was measured at the current density of (1) (T95). The results are shown in table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.
[ Table 1]
As shown in table 1 above, examples 1-1 to 1-9, using the compound of chemical formula 1 and the compound of chemical formula 2 of the present invention for an electron blocking layer and an electron transporting layer, respectively, showed characteristics of devices to which the compounds represented by chemical formulas 1 and 2 were applied together.
Comparative examples 2 to 11 are those in which the compound of chemical formula 1 is used instead of EB-1 or the compound of chemical formula 2 is used instead of HB-1 in comparative example 1, showing the characteristics of devices using only the compound represented by chemical formula 1 or only the compound represented by chemical formula 2.
The organic light emitting devices of experimental examples 1-1 to 1-9 basically exhibited low voltage, high efficiency and long life characteristics as compared to comparative examples 1 to 14, and in particular, the compound of chemical formula 1 had high efficiency characteristics and the compound of chemical formula 2 had long life characteristics.
Specifically, the devices of experimental examples 1-1 to 1-9 showed results of about 25% maximum improvement in luminous efficiency and about 115% maximum increase in lifetime, as compared with the comparative examples.
From this, it was confirmed that the compound of chemical formula 1 of the present invention can maintain the long-life characteristics of the organic light emitting device while having high efficiency characteristics when the compound of chemical formula 2 of the present invention is used as an electron blocking layer material and the compound of chemical formula 2 of the present invention is combined as an electron transport layer.
The preferred embodiment of the present invention (combination of the electron blocking layer compound and the electron injection and transport layer compound) is described above, but the present invention is not limited thereto, and the present invention can be modified into various forms within the scope of the claims of the present invention and the scope of the detailed description of the present invention, and the present invention also falls within the scope of the present invention.
Claims (14)
1. An organic light emitting device comprising:
a first electrode;
a second electrode;
a light emitting layer disposed between the first electrode and the second electrode;
a first organic layer disposed between the first electrode and the light emitting layer; and
a second organic layer disposed between the second electrode and the light emitting layer,
wherein the first organic layer includes a compound represented by the following chemical formula 1, and
the second organic layer includes a compound represented by the following chemical formula 2:
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
ar1 and Ar2, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
r1 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,
n is an integer of 1 to 8, and when n is 2 or more, 2 or more R1 may be the same or different from each other,
chemical formula 2
In the chemical formula 2,
l is a direct bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkoxy group having a valence of 2, a substituted or unsubstituted alkenyl group having a valence of 2, or a substituted or unsubstituted heteroarylene group,
ar3 and Ar4, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted arylalkyl, a substituted or unsubstituted arylalkenyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl,
x1 is N or CR11, X2 is N or CR12, X3 is N or CR13,
at least one of X1 to X3 is N,
r11 to R13 are the same as or different from each other, and each independently is hydrogen, deuterium, cyano, nitro, hydroxyl, carbonyl, ester group, imide group, amide group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkylsulfonyl group, substituted or unsubstituted arylsulfonyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted silyl group, substituted or unsubstituted boron group, substituted or unsubstituted amine group, substituted or unsubstituted arylphosphine group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group.
2. The organic light emitting device according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1 or 1-2:
chemical formula 1-1
Chemical formula 1-2
In the chemical formulas 1-1 and 1-2, Ar1, Ar2, R1 and n are defined as in the chemical formula 1.
3. The organic light emitting device according to claim 1, wherein the chemical formula 2 is represented by any one of the following chemical formulae 2-1 to 2-4:
chemical formula 2-1
Chemical formula 2-2
Chemical formula 2-3
Chemical formula 2-4
In the chemical formulae 2-1 to 2-4, L, Ar3, Ar4, and X1 to X3 are defined as same as those in the chemical formula 2.
4. The organic light emitting device according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-3 to 1-6:
chemical formulas 1 to 3
Chemical formulas 1 to 4
Chemical formulas 1 to 5
Chemical formulas 1 to 6
In the chemical formulas 1-3 to 1-6, Ar1 and Ar2 are defined as same as those in the chemical formula 1,
g1 and G2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
g1 is an integer from 1 to 10,
g2 is an integer from 1 to 8,
when G1 is 2 or more, 2 or more G1 s are the same or different from each other, and when G2 is 2 or more, 2 or more G2 s are the same or different from each other.
5. The organic light-emitting device according to claim 1, wherein Ar1 and Ar2, which are the same as or different from each other, are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted fluorenyl group.
6. The organic light emitting device of claim 1, wherein L is a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
7. The organic light-emitting device according to claim 1, wherein the Ar1 and Ar2 are the same as or different from each other, and each is independently an aryl group substituted or unsubstituted with an alkyl group or an aryl group.
8. The organic light emitting device according to claim 1, wherein the chemical formula 1 is represented by any one of the following compounds:
9. the organic light emitting device according to claim 1, wherein the chemical formula 2 is represented by any one of the following compounds:
10. the organic light emitting device according to claim 1, wherein the first organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer comprises the compound represented by chemical formula 1.
11. The organic light emitting device according to claim 1, wherein the second organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer comprises the compound represented by chemical formula 2.
12. The organic light emitting device according to claim 1, wherein the first organic layer comprises an electron blocking layer comprising the compound represented by chemical formula 1.
13. The organic light emitting device according to claim 1, wherein the second organic layer comprises a hole blocking layer comprising the compound represented by chemical formula 2.
14. The organic light emitting device of claim 1, further comprising one or more organic layers of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.
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| KR20170071399A (en) * | 2015-12-15 | 2017-06-23 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
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| WO2018226036A1 (en) * | 2017-06-08 | 2018-12-13 | 주식회사 엘지화학 | Organic light emitting element |
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| KR20180137315A (en) * | 2017-06-16 | 2018-12-27 | 머티어리얼사이언스 주식회사 | Organic electroluminescent device |
| CN109748909B (en) * | 2017-11-02 | 2022-04-19 | 江苏三月科技股份有限公司 | Compound containing spiroxanthene fluorene and nitrogen-containing six-membered heterocycle, preparation method thereof and application thereof in organic electroluminescent device |
| CN111279502B (en) * | 2018-01-17 | 2023-08-04 | 株式会社Lg化学 | Organic light emitting device |
| CN109796442A (en) * | 2019-01-04 | 2019-05-24 | 南京邮电大学 | A kind of spiro fluorene xanthene type electron transport material and its preparation method and application |
-
2020
- 2020-08-13 KR KR1020200101906A patent/KR20210020829A/en not_active Application Discontinuation
- 2020-08-13 CN CN202080041475.9A patent/CN113994495A/en active Pending
- 2020-08-13 WO PCT/KR2020/010785 patent/WO2021029710A1/en active Application Filing
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2022
- 2022-07-21 KR KR1020220090484A patent/KR102630968B1/en active IP Right Grant
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180090688A1 (en) * | 2015-09-24 | 2018-03-29 | Lg Chem, Ltd. | Compound and organic electronic element comprising same |
| KR20170071399A (en) * | 2015-12-15 | 2017-06-23 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| WO2018226036A1 (en) * | 2017-06-08 | 2018-12-13 | 주식회사 엘지화학 | Organic light emitting element |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20210020829A (en) | 2021-02-24 |
| WO2021029710A1 (en) | 2021-02-18 |
| KR20220110144A (en) | 2022-08-05 |
| KR102630968B1 (en) | 2024-01-30 |
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