CN117480163A - Compound and organic light emitting device comprising the same - Google Patents
Compound and organic light emitting device comprising the same Download PDFInfo
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- CN117480163A CN117480163A CN202280042188.9A CN202280042188A CN117480163A CN 117480163 A CN117480163 A CN 117480163A CN 202280042188 A CN202280042188 A CN 202280042188A CN 117480163 A CN117480163 A CN 117480163A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 113
- 239000010410 layer Substances 0.000 claims description 229
- 239000000126 substance Substances 0.000 claims description 193
- -1 dibenzofuranyl group Chemical group 0.000 claims description 84
- 125000003118 aryl group Chemical group 0.000 claims description 78
- 238000002347 injection Methods 0.000 claims description 62
- 239000007924 injection Substances 0.000 claims description 62
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- 229910052805 deuterium Inorganic materials 0.000 claims description 57
- 239000012044 organic layer Substances 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
- 230000005525 hole transport Effects 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 150000002431 hydrogen Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 230000000903 blocking effect Effects 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 11
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000005605 benzo group Chemical group 0.000 claims description 8
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- 125000004336 3,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
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- 239000002019 doping agent Substances 0.000 description 15
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- 125000000623 heterocyclic group Chemical group 0.000 description 8
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- 230000000694 effects Effects 0.000 description 5
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
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- 230000000052 comparative effect Effects 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000005549 heteroarylene group Chemical group 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
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- 239000000203 mixture Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- VBQVHWHWZOUENI-UHFFFAOYSA-N 1-phenyl-2H-quinoline Chemical compound C1C=CC2=CC=CC=C2N1C1=CC=CC=C1 VBQVHWHWZOUENI-UHFFFAOYSA-N 0.000 description 3
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- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
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- 229910052741 iridium Inorganic materials 0.000 description 3
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [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 3
- SKLNPGGDKRKWKC-UHFFFAOYSA-N (2-chlorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC=C1Cl SKLNPGGDKRKWKC-UHFFFAOYSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-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
- 238000012546 transfer Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- 239000008096 xylene Substances 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
The present specification provides a compound of formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present specification claims priority from korean patent application No. 10-2021-0180871 filed to the korean patent office on day 12 and 16 of 2021, the entire contents of which are incorporated herein.
The present specification relates to a compound and an organic light emitting device including the same.
Background
As a representative example of the organic electronic device, there is an organic light emitting device. In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition to the ground state again.
Most of the materials used in the organic light emitting device are pure organic materials or complex compounds of organic materials and metal constituting complexes. The materials used in the organic light-emitting device may be classified into a hole-injecting material, a hole-transporting material, a light-emitting material, an electron-transporting material, an electron-injecting material, and the like according to the purpose. 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 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. As the light-emitting layer substance, a substance having both p-type property and n-type property, that is, a substance having a stable form in both of an oxidized state and a reduced state is preferable, and a substance having high light emission efficiency for converting it into light when an excitation is formed is preferable.
In order to fully develop the excellent characteristics of the organic light-emitting device, development of a substance constituting an organic layer in the device is continuously demanded.
Disclosure of Invention
Technical problem
The present specification relates to a compound and an organic light emitting device including the same.
Solution to the problem
An embodiment of the present specification provides a compound of the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
x1 to X3 are each CH or N, at least one of the above X1 to X3 is N,
ar1 and Ar2 are the same or different from each other and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
r1 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group,
r2 is hydrogen, deuterium, cyano, or substituted or unsubstituted aryl,
r3 is hydrogen, deuterium or cyano,
a is an integer of 1 to 4, and when a is 2 or more, R3 are the same or different from each other,
n is 3 or 4, and the number of the N is not limited,
in addition, an embodiment of the present specification provides an organic light emitting device, including: a first electrode, a second electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound.
Effects of the invention
The compounds described in the present specification can be used as materials for organic layers of organic light-emitting devices. When an organic light emitting device including the compound according to at least one embodiment is manufactured, an organic light emitting device having a low driving voltage and a long lifetime can be obtained.
In particular, when the compound of the present invention is used for an electron transport layer, an electron injection layer and a light-emitting layer, the effect of reducing the driving voltage of the device, increasing the efficiency of the device, and prolonging the lifetime can be obtained.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron injection and transport layer 8, and a cathode 4.
< description of symbols >
1: substrate board
2: anode
3: light-emitting layer
4: cathode electrode
5: hole injection layer
6: hole transport layer
7: light-emitting layer
8: electron injection and transport layers
Detailed Description
The present specification will be described in more detail below.
The present specification provides a compound of the following chemical formula 1. When the compound of the following chemical formula 1 is contained in the organic layer of the organic light-emitting device, the effect of reducing the driving voltage of the device, increasing the efficiency of the device, and prolonging the lifetime can be obtained.
In particular, the compound of the following chemical formula 1 contains 3 or 4 phenylene groups used as a linking group, so that thermal stability can be ensured. The organic light emitting device including the compound of chemical formula 1 of the present invention has 3 to 4 aryl linking groups between the imidazole group having good electron injection characteristics and the N-containing heterocyclic group having excellent electron transport ability, thereby facilitating the adjustment of the conjugation length to coordinate the electron transport balance.
In contrast, when the number n of phenylene groups used as the linking group is 5 or more, the molecular weight of the compound becomes large, and thus the thermal stability may be unstable. When the number N of phenylene groups used as the linking groups is 1 or 2, the distance between the imidazole group and the N-containing heterocyclic group is close, and the electron transport is unbalanced.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
x1 to X3 are each CH or N, at least one of the above X1 to X3 is N,
ar1 and Ar2 are the same or different from each other and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
r1 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group,
r2 is hydrogen, deuterium, cyano, or substituted or unsubstituted aryl,
r3 is hydrogen, deuterium or cyano,
a is an integer of 1 to 4, and when a is 2 or more, R3 are the same or different from each other,
n is 3 or 4.
In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is connected to the other member but also the case where another member exists between the two members.
In the present specification, when a certain component is referred to as "including" or "comprising" a certain component, unless otherwise specified, it means that other components may be further included, and not excluded.
Throughout the specification of the present application, the term "a combination thereof" included in a markush-type expression means a mixture or combination of one or more components selected from the group consisting of the components described in the markush-type expression.
Hereinafter, the substituents of the present specification will be described in detail, but are not limited thereto.
In the present description of the invention,represents a site of binding to another substituent or binding moiety.
In the present specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted or unsubstituted with 1 or more substituents selected from deuterium (-D), halogen group, nitrile group, nitro group, alkyl group, alkenyl group, cycloalkyl group, alkoxy group, amino group, silyl group, aryl group and heteroaryl group, or substituted with a substituent formed by joining 2 or more substituents among the above-exemplified substituents, or does not have any substituent.
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 alkyl group may be linear, branched or cyclic, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. According to one embodiment, the alkyl group has 1 to 40 carbon atoms. According to another embodiment, the above alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above 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, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isopropyl, 2-methyl-hexyl, 4-methyl-hexyl, and the like.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, the alkynyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples thereof include alkynyl groups such as ethynyl, propynyl, 2-methyl-2-propynyl, 2-butynyl, and 2-pentynyl, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl and the like, but not limited thereto.
In the present specification, the above-mentioned alkoxy group may be a straight chain, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 40. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like are possible, but not limited thereto.
The alkyl groups, alkoxy groups, and other substituents containing an alkyl moiety described herein are all included in straight or branched chain forms.
In the present specification, the amine group may be selected from the group consisting of-NH 2 The monoalkylamino group, dialkylamino group, N-alkylaryl amino group, monoarylamino group, diarylamino group, triarylamino group, N-arylheteroarylamino group, N-alkylheteroarylamino group, monoaheteroarylamino group and diheteroarylamino group are not particularly limited, but are preferably 1 to 30 in carbon number. Specific examples of the amine group include, but are not limited to, methylamino group, dimethylamino group, trimethylamine group, ethylamino group, diethylamino group, triethylamine group, phenylamino group, naphthylamino group, biphenylamino group, anthracenylamino group, 9-methyl-anthracenylamino group, diphenylamino group, xylylamino group, N-phenyltolylamino group, triphenylamino group, N-phenylbiphenylamino group, N-phenylnaphthylamino group, N-biphenylnaphthylamino group, N-naphthylfluorenylamino group, N-phenylphenanthrylamino group, N-biphenylphenanthrenylamino group, N-phenylfluorenylamino group, N-phenylterphenylamino group, N-phenanthrenylfluolamino group, N-biphenylfluorenylamino group and the like.
In the present specification, the silyl group may be represented by-SiY a Y b Y c The chemical formula of (A) is shown in the specification, Y is shown in the specification a 、Y b And Y c Each may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Above-mentionedSpecific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc., but are 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 phenyl, biphenyl, terphenyl, or tetrabiphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenyl,A group, a fluorenyl group, a triphenylene group, and the like, but is not limited thereto.
In this specification, the above fluorenyl group may be substituted, and 2 substituents may be bonded to each other to form a spiro structure.
In the case where the above fluorenyl group is substituted, it may be(spirofluorenyl, spirobifluorenyl), -/->Substituted fluorenyl such as (9, 9-diphenylfluorenyl), but not limited thereto.
The aryl group may be substituted with an alkyl group to function as an arylalkyl group. The alkyl group may be selected from the above-mentioned examples.
In the present specification, a heteroaryl group is an aromatic ring group containing 1 or more heteroatoms which are non-carbon atoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, P, se, S and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heteroaryl group has a carbon numberFrom 2 to 30. The heteroaryl groups may be monocyclic or polycyclic. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,An azolyl group,Diazolyl, pyridyl, pyrimidinyl, triazinyl, triazolyl, quinolinyl, quinazolinyl, carbazolyl, benzo +.>Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, phenanthroline (phenanthrinyl), iso->Oxazolyl, thiadiazolyl, benzonaphthofuranyl, benzonaphthocarbazolyl, benzonaphthothienyl, and the like, but are not limited thereto.
In the present specification, arylene means a group having two bonding positions on an aryl group, i.e., a 2-valent group. They are each a 2-valent group, and the above description of aryl groups can be applied.
In the present specification, heteroarylene refers to a group having two binding sites on the heteroaryl group, i.e., a 2-valent group. They may be suitable for the description of heteroaryl groups described above, except that each is a 2-valent group.
In this specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on an atom substituted by the substituent. For example, 2 substituents substituted in the benzene ring at the ortho (ortho) position and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a hydrocarbon ring or a heterocyclic ring.
The hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic group and an aliphatic group, and may be selected from the cycloalkyl group or the aryl group, in addition to the 2-valent group.
The heterocyclic ring may be used as described for the heteroaryl group, except that it is 2-valent.
In one embodiment of the present specification, each of the above X1 to X3 is CH or N, and at least two of the above X1 to X3 are N.
In one embodiment of the present specification, X1 to X3 are N.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is 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.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is 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.
In an embodiment of the present specification, ar1 and Ar2 mentioned above are the same or different from each other and 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 anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzimidazolyl group, or a substituted or unsubstituted benzo group An azole group.
In one embodiment of the present specification, ar1 and Ar1 as described aboveAr2 are the same as or different from each other and 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 fluoranthenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted benzimidazolyl group, or a substituted or unsubstituted benzo groupAn azole group.
In one embodiment of the present specification, ar1 and Ar2 mentioned above are the same or different from each other, and are each independently deuterium, cyano, CF 3 Phenyl substituted or unsubstituted with alkyl, cycloalkyl, aryl or heteroaryl; a biphenyl group; a terphenyl group; naphthyl substituted or unsubstituted with aryl; phenanthryl; triphenylene; a fluoranthenyl group; dibenzofuranyl substituted or unsubstituted with aryl; dibenzothienyl substituted with aryl or unsubstituted; carbazolyl substituted or unsubstituted with aryl; a pyridyl group; benzimidazolyl substituted or unsubstituted with alkyl; or benzo substituted or unsubstituted with aryl An azole group.
In one embodiment of the present specification, ar1 and Ar2 mentioned above are the same or different from each other, and are each independently deuterium, cyano, CF 3 Methyl, ethyl, propyl, butyl, tert-butyl, cyclohexyl, adamantyl, phenyl, naphthyl or heteroaryl substituted or unsubstituted phenyl; a biphenyl group; naphthyl substituted or unsubstituted by phenyl; phenanthryl; dibenzofuranyl; dibenzothienyl; a carbazolyl group substituted or unsubstituted with a phenyl group; a pyridyl group; benzimidazolyl substituted or unsubstituted with methyl; or benzo substituted or unsubstituted with phenylAn azole group.
In one embodiment of the present specification, R1 is a substituted or unsubstituted alkyl group. In this case, the alkyl group may be linear, branched or cyclic as described above, and in particular, a cyclic alkyl group may be referred to as a cycloalkyl group. It is distinguished in that R1 may be defined as a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. Alkyl as defined in distinction to cycloalkyl refers to straight or branched chain alkyl, more specifically, R1 may be substituted or unsubstituted straight or branched chain alkyl, or substituted or unsubstituted cycloalkyl.
In one embodiment of the present specification, R1 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, R1 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms.
In one embodiment of the present specification, R1 is an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium, or a cycloalkyl group having 3 to 20 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present description, the above R1 is methyl or ethyl substituted or unsubstituted by deuterium, 2-diethyl ethyl substituted or unsubstituted by deuterium, n-propyl substituted or unsubstituted by deuterium, 2-dimethyl-3, 3-dimethyl-propyl substituted or unsubstituted by deuterium, n-butyl substituted or unsubstituted by deuterium, isobutyl substituted or unsubstituted by deuterium, tert-butyl substituted or unsubstituted by deuterium, sec-butyl substituted or unsubstituted by deuterium, 1-methyl-butyl substituted or unsubstituted by deuterium, n-ethyl-butyl substituted or unsubstituted by deuterium, n-pentyl substituted or unsubstituted by deuterium a deuterium-substituted or unsubstituted isopentyl group, a deuterium-substituted or unsubstituted neopentyl group, a deuterium-substituted or unsubstituted tert-amyl group, a deuterium-substituted or unsubstituted n-hexyl group, a deuterium-substituted or unsubstituted 1-methylpentyl group, a deuterium-substituted or unsubstituted 2-methylpentyl group, a deuterium-substituted or unsubstituted 4-methyl-2-pentyl group, a deuterium-substituted or unsubstituted 3, 3-dimethylpentyl group, a deuterium-substituted or unsubstituted 3, 3-dimethylbutyl group, a deuterium-substituted or unsubstituted 2-ethylbutyl group, a deuterium-substituted or unsubstituted heptyl group, a deuterium-substituted or unsubstituted n-heptyl group, a deuterium-substituted or unsubstituted 1-methylhexyl group, a deuterium-substituted or unsubstituted cyclohexyl group, or a deuterium-substituted or unsubstituted adamantyl group.
In one embodiment of the present specification, R1 is methyl substituted or unsubstituted by deuterium, ethyl substituted or unsubstituted by deuterium, propyl substituted or unsubstituted by deuterium, isopropyl substituted or unsubstituted by deuterium, butyl substituted or unsubstituted by deuterium, tert-butyl substituted or unsubstituted by deuterium, pentyl substituted or unsubstituted by deuterium, 2-dimethylpropyl substituted or unsubstituted by deuterium, 3-dimethylbutyl substituted or unsubstituted by deuterium, 3-dimethylpentyl substituted or unsubstituted by deuterium, 2-dimethyl-3, 3-dimethylpropyl substituted or unsubstituted by deuterium, 2-diethylethyl substituted or unsubstituted by deuterium, cyclohexyl, or adamantyl.
In one embodiment of the present specification, R1 is deuterium-substituted or unsubstituted methyl, deuterium-substituted or unsubstituted ethyl, propyl, isopropyl, deuterium-substituted or unsubstituted butyl, tert-butyl, pentyl, 2-dimethylpropyl, deuterium-substituted 3, 3-dimethylbutyl, 3-dimethylpentyl, 2-dimethyl-3, 3-dimethylpropyl, 2-diethylethyl, cyclohexyl, or adamantyl.
In one embodiment of the present specification, R2 is hydrogen, deuterium, cyano, or substituted or unsubstituted aryl having 6 to 60 carbon atoms.
In one embodiment of the present specification, R2 is hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted anthryl.
In one embodiment of the present specification, R2 is hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, or substituted or unsubstituted naphthyl.
In one embodiment of the present specification, R2 is hydrogen, deuterium, cyano, phenyl or naphthyl.
In one embodiment of the present description, n is 3 or 4.
In one embodiment of the present description, n is 3.
In one embodiment of the present description, n is 4.
In one embodiment of the present specification, the chemical formula 1 may be the following chemical formula 1-1 or 1-2.
[ chemical formula 1-1]
[ chemical formulas 1-2]
In the above chemical formula 1-1 and chemical formula 1-2,
x1 to X3, ar1, ar2, R1 and R2 are as defined in the above chemical formula 1,
r31 to R33 and R41 to R44 are as defined for R3 of formula 1 above,
a1 to a3 and b1 to b4 are each integers of 1 to 4, and when a1 to a3 and b1 to b4 are 2 or more, the structures in parentheses of 2 or more are the same or different from each other.
In an embodiment of the present specification, the above chemical formula 1-1 may be any one of the following chemical formulas 1-1-1 to 1-1-27.
[ chemical formulas 1-1-1]
[ chemical formulas 1-1-2]
[ chemical formulas 1-1-3]
[ chemical formulas 1-1-4]
[ chemical formulas 1-1-5]
[ chemical formulas 1-1-6]
[ chemical formulas 1-1-7]
[ chemical formulas 1-1-8]
[ chemical formulas 1-1-9]
[ chemical formulas 1-1-10]
[ chemical formulas 1-1-11]
[ chemical formulas 1-1-12]
[ chemical formulas 1-1-13]
[ chemical formulas 1-1-14]
[ chemical formulas 1-1-15]
[ chemical formulas 1-1-16]
[ chemical formulas 1-1-17]
[ chemical formulas 1-1-18]
[ chemical formulas 1-1-19]
[ chemical formulas 1-1-20]
[ chemical formulas 1-1-21]
[ chemical formulas 1-1-22]
[ chemical formulas 1-1-23]
[ chemical formulas 1-1-24]
[ chemical formulas 1-1-25]
[ chemical formulas 1-1-26]
[ chemical formulas 1-1-27]
In the above chemical formulas 1-1-1 to 1-27,
x1 to X3, ar1, ar2, R1 and R2 are as defined in the above chemical formula 1,
r31 to R33 are as defined for R3 of the above chemical formula 1,
a1 to a3 are each integers of 1 to 4, R31 are the same or different from each other when a1 is 2 or more, R32 are the same or different from each other when a2 is 2 or more, and R33 are the same or different from each other when a3 is 2 or more.
In an embodiment of the present specification, the above chemical formula 1-2 may be any one of the following chemical formulas 1-2-1 to 1-2-50.
[ chemical formula 1-2-1]
[ chemical formulas 1-2-2]
[ chemical formulas 1-2-3]
[ chemical formulas 1-2-4]
[ chemical formulas 1-2-5]
[ chemical formulas 1-2-6]
[ chemical formulas 1-2-7]
[ chemical formulas 1-2-8]
[ chemical formulas 1-2-9]
[ chemical formulas 1-2-10]
[ chemical formulas 1-2-11]
[ chemical formulas 1-2-12]
[ chemical formulas 1-2-13]
[ chemical formulas 1-2-14]
[ chemical formulas 1-2-15]
[ chemical formulas 1-2-16]
[ chemical formulas 1-2-17]
[ chemical formulas 1-2-18]
[ chemical formulas 1-2-19]
[ chemical formulas 1-2-20]
[ chemical formulas 1-2-21]
[ chemical formulas 1-2-22]
[ chemical formulas 1-2-23]
[ chemical formulas 1-2-24]
[ chemical formulas 1-2-25]
[ chemical formulas 1-2-26]
[ chemical formulas 1-2-27]
[ chemical formulas 1-2-28]
[ chemical formulas 1-2-29]
[ chemical formulas 1-2-30]
[ chemical formulas 1-2-31]
[ chemical formulas 1-2-32]
[ chemical formulas 1-2-33]
[ chemical formulas 1-2-34]
[ chemical formulas 1-2-35]
[ chemical formulas 1-2-36]
[ chemical formulas 1-2-37]
[ chemical formulas 1-2-38]
[ chemical formulas 1-2-39]
[ chemical formulas 1-2-40]
[ chemical formulas 1-2-41]
[ chemical formulas 1-2-42]
[ chemical formulas 1-2-43]
[ chemical formulas 1-2-44]
[ chemical formulas 1-2-45]
[ chemical formulas 1-2-46]
[ chemical formulas 1-2-47]
[ chemical formulas 1-2-48]
[ chemical formulas 1-2-49]
[ chemical formulas 1-2-50]
In the above chemical formulas 1-2-1 and 1-2-50,
x1 to X3, ar1, ar2, R1 and R2 are as defined in the above chemical formula 1,
r41 to R44 are as defined for R3 of the above chemical formula 1,
each of b1 to b4 is an integer of 1 to 4, R41 are the same or different from each other when b1 is 2 or more, R42 are the same or different from each other when b2 is 2 or more, R43 are the same or different from each other when b3 is 2 or more, and R44 are the same or different from each other when b4 is 2 or more.
In one embodiment of the present specification, the compound of formula 1 may be represented by any one of the following compounds.
The compound of chemical formula 1 in the present specification can produce a core structure as shown in the following reaction formula 1. The substituents may be combined by methods known in the art, and the kinds, positions and number of the substituents may be changed according to techniques known in the art.
[ reaction type 1]
In this specification, by introducing various substituents into the core structure as described above, compounds having various energy bandgaps can be synthesized. 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 structure shown above.
In addition, by introducing various substituents into the core structure of the structure shown above, a compound having the inherent characteristics of the introduced substituents can be synthesized. For example, a substance satisfying the conditions required for each organic layer can be synthesized by introducing substituents mainly used for the hole injection layer substance, the hole transport substance, the electron suppression substance, the light-emitting layer substance, and the electron transport layer substance used in manufacturing the organic light-emitting device into the above-described core structure.
In addition, an organic light emitting device according to the present specification, characterized by comprising: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the above-mentioned chemical formula 1.
The organic light-emitting device of the present specification can be manufactured by a general method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.
The compound may be used not only in the vacuum vapor deposition method but also in the solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
The organic layer of the organic light-emitting device of the present specification may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present specification may have a structure including a hole injection layer, a hole transport layer, a layer that performs hole transport and hole injection simultaneously, an electron blocking layer, a light emitting layer, an electron transport layer, and an electron injection layer, a layer that performs electron transport and electron injection simultaneously, and the like as organic layers. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller or larger number of organic layers.
In the organic light-emitting device of the present specification, the above-mentioned organic layer includes an electron transport layer containing the above-mentioned compound.
In the organic light emitting device of the present specification, the above-mentioned organic layer includes an electron injection layer containing the above-mentioned compound.
In the organic light-emitting device of the present specification, the above-mentioned organic layer includes a light-emitting layer containing the above-mentioned compound.
According to another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound as a host of the light-emitting layer.
According to another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound as a phosphorescent host of the light-emitting layer.
As another example, the organic layer includes a light-emitting layer including the compound as a host of the light-emitting layer, and may further include a dopant.
As another example, the organic layer includes a light-emitting layer including the compound as a host of the light-emitting layer, and may further include a dopant. The content of the above dopant may be contained in an amount of 1 to 20 parts by weight, more preferably, 1 to 5 parts by weight, with respect to 100 parts by weight of the host.
According to another embodiment, the organic layer includes a light emitting layer, and the light emitting layer may include the above-mentioned compound as a dopant of the light emitting layer.
In another embodiment, the organic layer includes a light-emitting layer including the compound as a dopant of the light-emitting layer, and may further include a host.
In another embodiment, the organic layer includes a light-emitting layer including the compound as a dopant of the light-emitting layer, including a fluorescent host or a phosphorescent host, and may include other organic compounds, metals, or metal compounds as dopants.
As another example, the organic layer includes a light emitting layer containing the compound as a dopant of the light emitting layer, including a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir) dopant.
In the organic light emitting device of the present specification, the above organic layer may include a hole injection layer or a hole transport layer, and the above hole injection layer or hole transport layer may contain the above-mentioned compound.
In the organic light emitting device of the present specification, the organic layer includes an electron blocking layer, and the electron blocking layer may include the compound described above.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
According to another embodiment, the first electrode is a cathode, and the second electrode is an anode.
For example, the above-described organic light emitting device may have a laminated structure as described 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 transport layer/light emitting layer/electron transport layer/cathode
(4) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(5) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(7) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(8) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(9) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(10) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(11) Anode/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/cathode
(12) Anode/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/electron injection layer/cathode
(13) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/cathode
(14) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/electron injection layer/cathode
(15) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole suppressing layer/cathode for simultaneous electron transport and electron injection
The structure of the organic light emitting device of the present specification may have the structure shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In the structure described above, the above-described compound may be contained in the above-described light-emitting layer 3.
Fig. 2 illustrates a structure of an organic light-emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron injection and transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1. In the structure described above, the above-described compound may be contained in the above-described hole injection layer 5, hole transport layer 6, light-emitting layer 7, or electron injection and transport layer 8.
For example, the organic light emitting device according to the present invention may be manufactured as follows: PVD (physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation) is used to vapor deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole suppressing layer, and a layer that performs electron transport and electron injection simultaneously is formed on the anode, and then a substance that can function as a cathode is vapor deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole suppression layer, a layer that performs both electron injection and electron transport, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that performs both hole injection and hole transport, or the like, but the organic layer is not limited to this and may have a single-layer structure. The organic layer may be formed into a smaller number of layers by a solvent process (solvent process) other than vapor deposition, such as spin coating, dip coating, knife coating, screen printing, ink jet printing, or thermal transfer printing, using various polymer materials.
The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and goldOr an alloy thereof; metal oxides such as zinc Oxide, indium Tin Oxide (ITO), and Indium zinc Oxide (IZO, indium Zinc Oxide); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
The cathode is an electrode for injecting electrons, and is preferably a substance having a small work function as a cathode substance in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that functions to smooth injection of holes from the anode to the light-emitting layer, and the hole injection substance is a substance that can well receive holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer.
According to an embodiment of the present specification, a compound of the following formula HI-1 may be used in the hole injection layer.
[HI-1]
In the case of the above-mentioned HI-1,
r201 to R205 are identical to or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted ring,
r206 is hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, R206 is an integer from 0 to 8, and R206 is 2 or more, R206 are the same or different from each other.
In one embodiment of the present description, R201 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or is combined with adjacent groups to form a substituted or unsubstituted ring.
In one embodiment of the present description, R201 is substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
In one embodiment of the present description, R201 is a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl.
In one embodiment of the present description, R201 is substituted or unsubstituted aryl.
In one embodiment of the present specification, R201 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, R201 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present description, R201 is substituted or unsubstituted phenyl.
In one embodiment of the present specification, R202 to R205 are the same or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
In one embodiment of the present specification, R202 to R205 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
In one embodiment of the present specification, R202 to R205 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
In one embodiment of the present disclosure, R202 and R204 are the same or different from each other and are each independently substituted or unsubstituted aryl.
In one embodiment of the present specification, R202 and R204 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, R202 and R204 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present disclosure, R202 and R204 are the same or different from each other and are each independently substituted or unsubstituted phenyl.
In one embodiment of the present description, R203 and R205 are the same or different from each other and are each independently a substituted or unsubstituted heteroaryl.
In one embodiment of the present description, R203 and R205 are the same or different from each other and are each independently a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
In one embodiment of the present description, R203 and R205 are the same or different from each other and are each independently a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.
In one embodiment of the present specification, R203 and R205 are the same or different from each other, and are each independently a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group.
In one embodiment of the present specification, R203 and R205 are the same or different from each other, and are each independently carbazolyl substituted or unsubstituted with aryl.
In one embodiment of the present specification, R203 and R205 are the same or different from each other, and are each independently a carbazolyl group substituted or unsubstituted with a phenyl group.
In one embodiment of the present description, R206 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group.
In one embodiment of the present disclosure, R206 is hydrogen or deuterium.
In one embodiment of the present specification, the above formula HI-1 is represented by the following compound.
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 a substance having a large mobility to the holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
According to an embodiment of the present specification, the hole transport layer may be provided as 1 layer or more or 2 layers or more. Specifically, when 2 hole transport layers are provided, a hole transport layer closer to the hole injection layer may be referred to as a first hole transport layer, and a hole transport layer closer to the light-emitting layer may be referred to as a second hole transport layer.
According to an embodiment of the present specification, the hole transport layer may include a compound represented by the following chemical formula HT-1, and specifically, the first hole transport layer may include a compound represented by the chemical formula HT-1, but is not limited thereto.
[ chemical formula HT-1]
In the above-mentioned chemical formula HT-1,
at least one of X '1 to X'6 is N, the remainder are CH,
r309 to R314 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or are combined with each other with an adjacent group to form a substituted or unsubstituted ring.
According to an embodiment of the present specification, X '1 to X'6 are N.
According to an embodiment of the present disclosure, R309 to R314 are cyano groups.
According to one embodiment of the present specification, the above formula HT-1 is represented by the following compounds.
The hole transport layer may include a compound of the following chemical formula HT-2, and specifically, the second hole transport layer may include a compound represented by the chemical formula HT-2, but is not limited thereto.
[ chemical formula HT-2]
In the above-mentioned chemical formula HT-2,
L101 is a direct bond, or a substituted or unsubstituted arylene,
r101 and R102 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
r103 and R104 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group,
when o is 1 or 2 and o is 2, the structures in brackets are the same or different from each other.
In one embodiment of the present specification, L101 is a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
In one embodiment of the present specification, L101 is a directly bonded or substituted or unsubstituted phenylene group.
In one embodiment of the present specification, L101 is a direct bond or phenylene group.
In one embodiment of the present specification, R101 and R102 are the same or different from each other and each independently is a substituted or unsubstituted aryl group.
In one embodiment of the present specification, R101 and R102 are the same or different from each other, and each is independently a substituted or unsubstituted monocyclic aryl group or a substituted or unsubstituted polycyclic aryl group.
In one embodiment of the present specification, R101 and R102 are the same or different from each other and 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 anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted fluorenyl group.
In one embodiment of the present specification, R101 and R102 are the same or different from each other, and each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group.
In one embodiment of the present specification, R101 and R102 are the same or different from each other, and each is independently phenyl substituted or unsubstituted with a carbazolyl substituted with phenyl, biphenyl, or fluorenyl substituted with an alkyl.
In one embodiment of the present specification, R101 and R102 are the same or different from each other, and each is independently phenyl substituted or unsubstituted with phenyl substituted carbazolyl.
In one embodiment of the present specification, R103 and R104 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group.
In one embodiment of the present specification, R103 and R104 are the same or different from each other, and each is independently an aryl group.
In one embodiment of the present specification, R103 and R104 are phenyl groups.
In one embodiment of the present specification, the above formula HT-2 is represented by the following compounds.
An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer is a layer that can prevent holes injected from the hole injection layer from passing through the light emitting layer to enter the electron injection layer, thereby improving the lifetime and efficiency of the device, and the above-described compound or materials known in the art can be used.
The light-emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. When the organic light emitting device includes an additional light emitting layer in addition to the light emitting layer including the compound represented by the above chemical formula 1, the additional light emitting layer may emit red, green, or blue light, and may be composed of a phosphorescent material or a fluorescent material. Specifically, there are 8-hydroxy-quinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
Examples of the host material of the light-emitting layer include an aromatic condensed ring derivative and a heterocyclic compound. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto.
As a host material of the light-emitting layer, a compound of the following chemical formula HO may be contained.
[ chemical formula HO ]
In the above-mentioned chemical formula HO,
l21 to L23 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
r21 to R27 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
Ar21 to Ar23 are the same as or different from each other, each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
k is 0 or 1.
In one embodiment of the present specification, when k is 0, hydrogen or deuterium is attached to the position of-L23-Ar 23.
In one embodiment of the present specification, L21 to L23 are the same or different from each other, each independently being a direct bond; a substituted or unsubstituted C6-C30 arylene group; or a substituted or unsubstituted C2-C30 heteroarylene group comprising N, O or S.
In one embodiment of the present specification, L21 to L23 are the same or different from each other, each independently being a direct bond; arylene of C6-C30; or C2-C30 heteroarylene containing N, O or S, which is substituted or unsubstituted with C1-C10 alkyl, C6-C30 aryl or C2-C30 heteroaryl.
In an embodiment of the present specification, L21 to L23 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted 2-valent dibenzofuranyl group, or a substituted or unsubstituted 2-valent dibenzothienyl group.
In one embodiment of the present specification, ar21 to Ar23 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group.
In one embodiment of the present specification, ar21 to Ar23 are the same as or different from each other, and are each independently a C6-C30 aryl group substituted or unsubstituted with deuterium, or a C2-C30 heteroaryl group substituted or unsubstituted with deuterium.
In one embodiment of the present specification, ar21 to Ar23 are the same or different from each other, each independently is a substituted or unsubstituted monocyclic to tetracyclic aryl group, or a substituted or unsubstituted monocyclic to tetracyclic heteroaryl group.
In an embodiment of the present specification, ar21 to Ar23 are the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic to tetracyclic aryl group substituted with deuterium, or a substituted or unsubstituted monocyclic to tetracyclic heteroaryl group substituted with deuterium.
In an embodiment of the present specification, ar21 to Ar23 are the same or different from each other and 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 anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenacyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted naphthobenzothienyl group.
In an embodiment of the present specification, ar21 and Ar22 are different from each other.
In one embodiment of the present disclosure, ar21 is a substituted or unsubstituted aryl group and Ar22 is a substituted or unsubstituted aryl group.
In one embodiment of the present disclosure, ar21 is a substituted or unsubstituted aryl group and Ar22 is a substituted or unsubstituted heteroaryl group.
In one embodiment of the present disclosure, ar21 is a deuterium-substituted or unsubstituted aryl group, and Ar22 is a deuterium-substituted or unsubstituted aryl group.
In one embodiment of the present disclosure, ar21 is aryl substituted or unsubstituted with deuterium, and Ar22 is heteroaryl substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R21 to R27 are the same or different from each other, and are each independently hydrogen or deuterium.
In one embodiment of the present description, R21 to R27 are hydrogen.
In one embodiment of the present description, R21 to R27 are deuterium.
In one embodiment of the present specification, the above formula HO is represented by the following formula HO 1.
[ chemical formula HO1]
In the above-mentioned chemical formula HO1,
the definitions of L21 to L23 and Ar21 to Ar23 are the same as those in the chemical formula HO, D represents deuterium, k1 is an integer of 0 to 8, and k2 is an integer of 0 to 7.
In one embodiment of the present specification, the compound represented by the above formula HO is any one selected from the following compounds.
In an embodiment of the present disclosure, the weight ratio of the host to the dopant may be 95:5 to 5:95.
In an embodiment of the present disclosure, the weight ratio of the host to the dopant may be 1:9 to 9:1, 2:8 to 8:2, 3:7 to 7:3, or 4:6 to 6:4, preferably may be 5:5 (1:1).
In one embodiment of the present specification, the light-emitting layer includes 1 or 2 or more compounds represented by the chemical formula HO.
When the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent substance such as PIQIr (acac) (bi (1-phenylisoquinoline) acetylacetonide), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium), bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) irium, tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin), or Alq may be used 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum, etc., but not limited thereto. When the light emitting layer emits green light, ir (ppy) can be used as a light emitting dopant 3 Phosphorescent substances such as (factris (2-phenylpyridine) iridium, planar tris (2-phenylpyridine) iridium), or Alq 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum), but are not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, (4, 6-F 2 ppy) 2 Examples of the fluorescent substance include, but are not limited to, phosphorescent substances such as Irpic, fluorescent substances such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers.
In one embodiment of the present disclosure, the dopant of the light emitting layer may include a pyrene compound, and specifically, the pyrene compound may be a compound of the following chemical formula D1.
[ chemical formula D1]
In the above chemical formula D1, ar11 to Ar14 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, ar11 and Ar13 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group.
In one embodiment of the present specification, ar11 and Ar13 are the same or different from each other, and each is independently an aryl group substituted or unsubstituted with a silyl group.
In one embodiment of the present specification, ar11 and Ar13 are the same as or different from each other, and each is independently a trimethylsilyl-substituted or unsubstituted terphenyl group.
In one embodiment of the present description, ar12 and Ar14 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group.
In one embodiment of the present description, ar12 and Ar14 are the same or different from each other, and are each independently a substituted or unsubstituted phenyl group.
In one embodiment of the present disclosure, ar12 and Ar14 are phenyl groups.
In an embodiment of the present specification, ar11 and Ar13 may be the same as each other.
In an embodiment of the present specification, ar12 and Ar14 may be the same as each other.
In one embodiment of the present specification, the compound of formula D1 may be the following compound.
A hole-suppressing layer may be provided between the electron-transporting layer and the light-emitting layer, and the hole-suppressing layer is a layer that prevents holes from reaching the cathode, and may be formed under the same conditions as the hole-injecting layer. Specifically, as the hole-inhibiting substance, triazine derivatives, phenanthroline derivatives, BCP, and the like are mentioned, but the hole-inhibiting substance is not limited thereto, and materials known in the art can be used.
The electron transport layer can play a role in enabling electron transport to be smooth. The electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high mobility of electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The thickness of the electron transport layer may be 1nm to 50nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the degradation of the electron transport property can be prevented, and when it is 50nm or less, there is an advantage that the increase of the driving voltage for improving the migration of electrons can be prevented when the thickness of the electron transport layer is too thick.
The electron injection layer can perform a function of smoothly injecting electrons. As the electron injecting substance, the following compounds are preferable: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the invention
Hereinafter, the present specification will be described in more detail by examples. However, the following examples are only for illustrating the present specification, and are not intended to limit the present specification.
Synthesis example
Synthesis example 1: synthesis of Compound 1
Step 1) Synthesis of Compound 1-a
1- (3-bromophenyl) -2-ethyl-1H-benzo [ d ] under nitrogen atmosphere]Imidazole (50 g,166mm ol) and (2-chlorophenyl) boronic acid (26 g,166 mmol) were added to 1000ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (68.8 g,498 mmol) was dissolved in 69ml of water and charged, and after stirring well, tetrakis (triphenylphosphine) palladium (5.8 g,5 mmol) was charged. After 1 hour of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. This was again poured into 1105mL of toluene (20 times the theoretical yield of Compound 1-a) and dissolved, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to give compound 1-a (47 g,85%, MS: [ M+H) as a white solid ] + ＝333.8)。
Step 2) Synthesis of Compound 1
The compounds 1-a (20 g,60.1 mmol) and 2, 4-diphenyl-6- (2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine (26.2 g,60.1 mmol) were added to 400ml of 1, 4-bis under nitrogenStirring and refluxing the mixture in alkane. ThenPotassium phosphate (38.3 g,180.3 mmol) was dissolved in 38ml of water and charged, and after stirring thoroughly, bis (dibenzylideneacetone) palladium (1 g,1.8 mmol) and tricyclohexylphosphine (1 g,3.6 mmol) were charged. After the reaction was carried out for 8 hours, the resultant solid was filtered after cooling to room temperature. The solid was poured into 1091mL of toluene (30 times the theoretical amount of compound 1) and dissolved, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to yield compound 1 (5.5 g,15%, MS: [ M+H) as a white solid] + ＝606.3)。
Synthesis example 2: synthesis of Compound 2
In Synthesis example 1, 1- (3-bromophenyl) -2-ethyl-1H-benzo [ d ]]Imidazole, (2-chlorophenyl) boronic acid and 2, 4-diphenyl-6- (2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine were modified to 1- (3-bromophenyl) -2- (ethyl-d 5) -1H-benzo [ d ] ]Imidazole-4, 5,6,7-d4, (3-chlorophenyl) boric acid and 4, 6-diphenyl-2- (3- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) pyrimidine were used, and Compound 2 (MS [ M+H ] was produced by the same production method as that of Compound 1] + ＝614.3)。
Synthesis example 3: synthesis of Compound 3
In synthesis example 1, (2-chlorophenyl) boric acid and 2, 4-diphenyl-6- (2- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) phenyl) -1,3, 5-triazine were changed to (3-chlorophenyl 1) boric acid and 2, 4-bis (naphthalen-1-yl) -6- (3- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) phenyl) -1,3, 5-triazine, and compound 3 (MS [ M+H ] was produced by the same production method as that of compound 1] + ＝706.3)。
Synthesis example 4: synthesis of Compound 4
In synthetic example 1, compound 4 (MS [ M+H ] was produced by the same production method as that of compound 1, except that (2-chlorophenyl) boric acid and 2, 4-diphenyl-6- (2- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) phenyl) -1,3, 5-triazine were changed to (3-chloro-5-cyanophenyl) boric acid and 4, 6-diphenyl-2- (3- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) phenyl) pyrimidine and used ] + ＝630.3)。
Synthesis example 5: synthesis of Compound 5
Step 1) Synthesis of Compound 5-a
2-bromo-4 '-chloro- [1,1' -biphenyl ] under nitrogen atmosphere]-4-carbonitrile (50 g,170.9 mmol) and 2, 4-diphenyl-6- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine (74.4 g,170.9 mmol) were added to 1000ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (70.9 g,512.7 mmol) was dissolved in 71ml of water and the mixture was stirred well, and tetrakis (triphenylphosphine) palladium (5.9 g,5.1 mmol) was added thereto. After 3 hours of reaction, the organic layer was separated from the aqueous layer after cooling to room temperature, and the organic layer was distilled. This was again put into 1778mL of toluene (20 times the theoretical yield of compound 5-a) and dissolved, and after washing 2 times with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to give 5-a (75.6 g,85%, MS: [ M+H) as a white solid compound] + ＝521.2)。
Step 2) Synthesis of Compound 5
Compound 5-a (50 g,96 mmol) and 4- (2-ethyl-1H-benzo [ d) are reacted under nitrogen]Imidazol-6-yl) benzylNitrile (23.7 g,96 mmol) was added to 1000ml of xylene, stirred and refluxed. Then, sodium t-butoxide (27.7 g,287.9 mmol) was added thereto, and after stirring thoroughly, bis (tri-t-butylphosphine) palladium (1.5 g,2.9 mmol) was added thereto. After 3 hours of reaction, the organic layer was cooled to room temperature, filtered to remove alkali, and the filtered organic layer was distilled. This was again poured into 702mL of chloroform (10 times the theoretical yield of Compound 5) and dissolved, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate, whereby white solid compound 5 (54 g,77%, MS: [ M+H) was produced ] + ＝732.3)。
Synthesis example 6: synthesis of Compound 6
In Synthesis example 1, 1- (3-bromophenyl) -2-ethyl-1H-benzo [ d ]]Imidazole, (2-chlorophenyl) boronic acid and 2, 4-diphenyl-6- (2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine are modified to 2-bromo-5-chloro-p-phthalonitrile, 2- (dibenzo [ b, d)]Furan-3-yl) -4-phenyl-6- (3- (4, 5-tetramethyl-1, 3, 2-) -dioxaborolan-2-yl) phenyl) -1,3, 5-triazine and 2-ethyl-1- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1H-benzo [ d ]]Imidazole was used, and except for this, compound 6 (MS [ m+h] + ＝746.3)。
Synthesis example 7: synthesis of Compound 7
In Synthesis example 1, 1- (3-bromophenyl) -2-ethyl-1H-benzo [ d ]]Imidazole and (2-chlorophenyl) boronic acid were changed to 1- (4-bromophenyl) -2-ethyl-1H-benzo [ d ]]Imidazole and (2 '-chloro- [1,1' -biphenyl)]-3-yl) boric acid, except for using the same method as the production method of compound 1The production method of Compound 7 (MS [ M+H)] + ＝682.3)。
Synthesis example 8: synthesis of Compound 8
In Synthesis example 1, 1- (3-bromophenyl) -2-ethyl-1H-benzo [ d ]]Imidazole, (2-chlorophenyl) boronic acid and 2, 4-diphenyl-6- (2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine are modified to 1- (4-bromophenyl) -2-ethyl-1H-benzo [ d ] ]Imidazole, (2 '-chloro- [1,1' -biphenyl)]-4-yl) boric acid and 2- (2- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) phenyl) -4, 6-di-p-tolyl-1, 3, 5-triazine were used, and Compound 8 (MS [ M+H ] was produced by the same production method as that of Compound 1] + ＝710.3)。
Synthesis example 9: synthesis of Compound 9
In Synthesis example 1, 1- (3-bromophenyl) -2-ethyl-1H-benzo [ d ]]Imidazole, (2-chlorophenyl) boronic acid and 2, 4-diphenyl-6- (2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine are modified to 1- (2-bromophenyl) -2-methyl-1H-benzo [ d ]]Imidazole, (2 '-chloro- [1,1' -biphenyl)]-2-yl) boronic acid and 2, 4-di ([ 1,1' -biphenyl)]-3-yl) -6- (2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine was used, except that compound 9 (MS [ M+H ] was produced by the same production method as that of compound 1] + ＝820.3)。
Synthesis example 10: synthesis of Compound 10
In Synthesis example 1, 1- (3-bromophenyl) -2-ethyl-1H-benzo [ d ]]Imidazole and (2-chlorobenzeneGroup) boric acid is changed into 3-bromo-4-chlorobenzonitrile and 2-ethyl-1- (3 '- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) - [1,1' -biphenyl)]-3-yl) -1H-benzo [ d ] ]Imidazole was used, and except for this, compound 10 (MS [ m+h] + ＝707.3)。
Synthesis example 11: synthesis of Compound 11
In Synthesis example 1, 1- (3-bromophenyl) -2-ethyl-1H-benzo [ d ]]Imidazole, (2-chlorophenyl) boronic acid and 2, 4-diphenyl-6- (2- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) phenyl) -1,3, 5-triazine modification to 2-bromo-5-chloro-p-phthalonitrile, 2-ethyl-1- (4 '- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) - [1,1' -biphenyl]-4-yl) -1H-benzo [ d ]]Imidazole and 2, 4-bis (naphthalen-1-yl) -6- (2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine were used, and compound 11 (MS [ M+H ] was produced by the same production method as that of compound 1] + ＝832.3)。
Synthesis example 12: synthesis of Compound 12
In Synthesis example 1, 1- (3-bromophenyl) -2-ethyl-1H-benzo [ d ]]Imidazole, (2-chlorophenyl) boronic acid and 2, 4-diphenyl-6- (2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine were modified to 1- (2-bromophenyl) -2-isopropyl-1H-benzo [ d ]]Imidazole, (4 '-chloro- [1,1' -biphenyl)]-4-yl) boronic acid and 3'- (4-phenyl-6- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazin-2-yl) - [1,1' -biphenyl ] ]4-formonitrile was used, and compound 12 (MS [ M+H ] was produced by the same production method as that of compound 1 except that] + ＝797.3)。
Experimental example 1
ITO (indium tin oxide) toThe glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following compound HI-A was usedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, hexanitrile hexaazatriphenylene (HAT,)>) And the following compound HT-A- >And a hole transport layer is formed.
Then, on the hole transport layer, the film thickness is set to beThe following compounds BH and BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer.
On the light-emitting layer, the compound 1 produced in Synthesis example 1 and the following compound [ LiQ ]]Vacuum evaporation was performed at a weight ratio of 1:1 to obtain a solution of lithium quinolineForm an electron injection and transport layer. On the electron transport and injection layer, lithium fluoride (LiF) is added in sequence +.>Is made of aluminum +.>And vapor deposition is performed to form a cathode. />
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathodeIs kept at>Is to maintain a vacuum degree of 1X 10 during vapor deposition -7 ～5×10 -8 The support is thus fabricated into an organic light emitting device.
Experimental examples 2 to 12
An organic light emitting device was manufactured by the same method as in experimental example 1, except that the compound of the following table 1 was used instead of the compound of experimental example 1.
Comparative examples 1 to 6
An organic light emitting device was manufactured by the same method as in experimental example 1, except that the compound of the following table 1 was used instead of the compound of experimental example 1. The compounds of ET-1 to ET-6 used in table 1 below are shown below.
The organic light-emitting devices manufactured in the above experimental examples and comparative experimental examples were subjected to a temperature of 10mA/cm 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20mA/cm 2 The time (T) at which the initial luminance was 90% was measured at the current density of (2) 90 ). The results are shown in table 1 below.
TABLE 1
As described in the above table 1, it was confirmed that when the compound represented by the chemical formula 1 of the present invention was used in an organic light emitting device, the compound was excellent in voltage, efficiency and/or lifetime (T 90 ) The above shows excellent characteristics.
Comparing experimental examples 1 to 12 of table 1 with comparative experimental examples 2 to 3, the organic light emitting device comprising the compound of chemical formula 1 of the present invention has 3 to 4 aryl linking groups between an imidazole group having good electron injection characteristics and an N-containing heterocyclic group having excellent electron transport ability, thereby facilitating the adjustment of the conjugation length to coordinate the electron transport balance. Therefore, it can be confirmed that the organic light emitting device, which is closely combined with the distance of the imidazole group and the N-containing heterocyclic group, shows significantly excellent characteristics in terms of efficiency and lifetime.
Comparing experimental examples 1 to 12 of table 1 with comparative experimental examples 1 and 4 to 6, it can be confirmed that the organic light emitting device including the compound of chemical formula 1 of the present invention shows significantly superior characteristics in terms of voltage and efficiency compared to an organic light emitting device having aryl groups in an imidazole group to enhance conjugation.
Claims (13)
1. A compound of the following chemical formula 1:
[ chemical formula 1]
In the chemical formula 1 described above, a compound having the formula,
x1 to X3 are each CH or N, at least one of the X1 to X3 is N,
ar1 and Ar2 are the same or different from each other and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
r1 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group,
r2 is hydrogen, deuterium, cyano, or substituted or unsubstituted aryl,
r3 is hydrogen, deuterium or cyano,
a is an integer of 1 to 4, and when a is 2 or more, R3 are the same or different from each other,
n is 3 or 4.
2. The compound of claim 1, wherein each of X1 to X3 is CH or N, and at least two of the X1 to X3 are N.
3. The compound according to claim 1, wherein Ar1 and Ar2 are the same or different from each other and 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 fluoranthenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted benzimidazolyl group, or a substituted or unsubstituted benzo group An azole group.
4. The compound of claim 1, wherein R1 is deuterium-substituted or unsubstituted methyl, deuterium-substituted or unsubstituted ethyl, deuterium-substituted or unsubstituted propyl, deuterium-substituted or unsubstituted isopropyl, deuterium-substituted or unsubstituted butyl, deuterium-substituted or unsubstituted tert-butyl, deuterium-substituted or unsubstituted pentyl, deuterium-substituted or unsubstituted 2, 2-dimethylpropyl, deuterium-substituted or unsubstituted 3, 3-dimethylbutyl, deuterium-substituted or unsubstituted 3, 3-dimethylpentyl, deuterium-substituted or unsubstituted 2, 2-dimethyl-3, 3-dimethylpropyl, deuterium-substituted or unsubstituted 2, 2-diethylethyl, cyclohexyl, or adamantyl.
5. The compound of claim 1, wherein R2 is hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, or substituted or unsubstituted naphthyl.
6. The compound of claim 1, wherein the chemical formula 1 is the following chemical formula 1-1 or chemical formula 1-2:
[ chemical formula 1-1]
[ chemical formulas 1-2]
In the chemical formulas 1-1 and 1-2,
x1 to X3, ar1, ar2, R1 and R2 are as defined in the chemical formula 1,
r31 to R33 and R41 to R44 are as defined for R3 of said chemical formula 1,
a1 to a3 and b1 to b4 are each integers of 1 to 4, and when a1 to a3 and b1 to b4 are 2 or more, structures in brackets of 2 or more are the same or different from each other.
7. The compound of claim 1, wherein the compound of formula 1 is any one of the following compounds:
8. an organic light emitting device comprising: a first electrode, a second electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 7.
9. The organic light-emitting device of claim 8, wherein the organic layer comprises an electron injection layer or an electron transport layer, the electron injection layer or the electron transport layer comprising the compound.
10. The organic light-emitting device of claim 8, wherein the organic layer comprises an electron blocking layer comprising the compound.
11. The organic light-emitting device of claim 8, wherein the organic layer comprises a light-emitting layer comprising the compound.
12. The organic light-emitting device according to claim 8, wherein the organic layer comprises a light-emitting layer containing the compound as a host of the light-emitting layer.
13. The organic light-emitting device according to claim 8, wherein the organic layer comprises a hole injection layer or a hole transport layer, the hole injection layer or the hole transport layer containing the compound.
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| KR20210180871 | 2021-12-16 | ||
| KR10-2021-0180871 | 2021-12-16 | ||
| PCT/KR2022/020645 WO2023113561A1 (en) | 2021-12-16 | 2022-12-16 | Compound and organic light-emitting device comprising same |
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| KR102659372B1 (en) * | 2016-03-04 | 2024-04-22 | 주식회사 동진쎄미켐 | Novel compound and organic electroluminescent device comprising the same |
| CN111247128B (en) * | 2018-03-22 | 2023-05-23 | 株式会社Lg化学 | Compound and organic light emitting diode comprising the same |
| TWI710621B (en) * | 2019-07-22 | 2020-11-21 | 昱鐳光電科技股份有限公司 | Naphthyl-substituted phenylpyrimidines compounds and organic electroluminescent devices using the same |
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