CN112585776A - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- CN112585776A CN112585776A CN201980054052.8A CN201980054052A CN112585776A CN 112585776 A CN112585776 A CN 112585776A CN 201980054052 A CN201980054052 A CN 201980054052A CN 112585776 A CN112585776 A CN 112585776A
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- 239000012044 organic layer Substances 0.000 claims abstract description 96
- 239000010410 layer Substances 0.000 claims description 316
- 239000000126 substance Substances 0.000 claims description 231
- 125000000623 heterocyclic group Chemical group 0.000 claims description 132
- 150000001875 compounds Chemical class 0.000 claims description 128
- 125000003118 aryl group Chemical group 0.000 claims description 122
- 125000001424 substituent group Chemical group 0.000 claims description 114
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 87
- 229910052805 deuterium Inorganic materials 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 80
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 239000001257 hydrogen Substances 0.000 claims description 63
- 150000002431 hydrogen Chemical group 0.000 claims description 55
- 125000005264 aryl amine group Chemical group 0.000 claims description 30
- 125000002560 nitrile group Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 239000002019 doping agent Substances 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000000732 arylene group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- -1 1-methylpentyl group Chemical group 0.000 description 114
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- 239000000243 solution Substances 0.000 description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 238000004519 manufacturing process Methods 0.000 description 41
- 238000002347 injection Methods 0.000 description 40
- 239000007924 injection Substances 0.000 description 40
- 230000032258 transport Effects 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 35
- 125000002950 monocyclic group Chemical group 0.000 description 35
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 32
- 230000005525 hole transport Effects 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 26
- 125000004432 carbon atom Chemical group C* 0.000 description 26
- 239000007787 solid Substances 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- 238000004949 mass spectrometry Methods 0.000 description 22
- 238000000034 method Methods 0.000 description 21
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 20
- 239000000463 material Substances 0.000 description 20
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- 150000002430 hydrocarbons Chemical group 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 230000000903 blocking effect Effects 0.000 description 16
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 16
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 16
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- 235000019270 ammonium chloride Nutrition 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 239000012047 saturated solution Substances 0.000 description 14
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 14
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
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- 125000001624 naphthyl group Chemical group 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 10
- 239000011368 organic material Substances 0.000 description 10
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 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 description 6
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- 150000001454 anthracenes Chemical class 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 125000005956 isoquinolyl group Chemical group 0.000 description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 5
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 5
- 125000005493 quinolyl group Chemical group 0.000 description 5
- 238000007738 vacuum evaporation Methods 0.000 description 5
- CEOHKQQUAYAZNB-UHFFFAOYSA-N 1-bromo-2,3-dichloro-5-methylbenzene Chemical compound CC1=CC(Cl)=C(Cl)C(Br)=C1 CEOHKQQUAYAZNB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 4
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
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- 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- 238000007740 vapor deposition Methods 0.000 description 4
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- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract
The present description provides an organic light emitting device including a first organic layer and a second organic layer.
Description
Technical Field
The present description relates to organic light emitting devices.
This application claims priority to korean patent application No. 10-2018-0147239, which was filed on 26.11.2018 from the korean patent office, the entire contents of which are incorporated herein by reference.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between two electrodes, holes are injected from an anode into an organic layer, electrons are injected from a cathode into the organic layer, an exciton (exiton) is formed when the injected holes and electrons meet, and light is emitted when the exciton falls back to a ground state.
There is a continuing demand for the development of new materials for organic light emitting devices as described above.
Disclosure of Invention
Technical problem
The present specification provides that the compound represented by chemical formula 1 is contained in the first organic layer and the compound represented by chemical formula 2 is contained in the second organic layer, thereby providing an organic light emitting device having a low driving voltage or high efficiency or excellent lifetime characteristics or high color purity.
Means for solving the problems
The present specification provides an organic light emitting device, comprising: an anode, a cathode, a first organic material layer and a second organic material layer provided between the anode and the cathode,
the first organic layer includes a compound represented by the following chemical formula 1,
the second organic layer includes a compound represented by the following chemical formula 2.
[ chemical formula 1]
In the above-described chemical formula 1,
x is B; p ═ O; or P is equal to S,
z1 to Z3, which may be the same or different from each other, are each independently a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring,
a1 is N (R101) or O, A2 is N (R102) or O,
r101 and R102 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring,
[ chemical formula 2]
In the above-described chemical formula 2,
y is O or S, and Y is O or S,
r21 to R24, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are represented by the following chemical formula 3, or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring,
at least one of R21 to R24 is represented by the following chemical formula 3,
r21 to R24 are the same or different and each independently an integer of 0 to 4, R21 is 2 or more, R21 are the same or different from each other, R22 is 2 or more, R22 is the same or different from each other, R23 is 2 or more, R23 is the same or different from each other, R24 is 2 or more, R24 is the same or different from each other,
[ chemical formula 3]
In the above-mentioned chemical formula 3,
x1 is N or C (R31), X2 is N or C (R32), X3 is N or C (R33), at least one of X1 to X3 is N,
r31, R32 and R33 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or forms a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring in combination with Ar1 or Ar2,
ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group substituted or unsubstituted with R41, or a heterocyclic group substituted or unsubstituted with R42, or combined with R31, R32, or R33 to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,
r41 and R42, which may be the same or different from each other, are each independently one member selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a halogenated alkyl group, an alkoxy group, a silyl group, an aryl group and a heterocyclic group, or a group in which 2 or more substituents are bonded to each other,
l is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,
m is an integer of 0 to 4, and when m is 2 or more, L's are the same or different from each other,
and a site binding to chemical formula 2.
Effects of the invention
An organic light emitting device according to an embodiment of the present specification includes a compound of chemical formula 1 and a compound of chemical formula 2, and thus has excellent characteristics of a long lifetime, a high efficiency, and a low driving voltage.
Drawings
Fig. 1 to 4 illustrate examples of the organic light emitting device of the present invention.
[ description of symbols ]
0: substrate
1: cathode electrode
2: electron transport layer
3: hole transport layer
4: anode
5: organic material layer
6: organic material layer
7: hole blocking layer or electron-regulating layer
11: light-emitting layer 1
12: light-emitting layer 2
13: light-emitting layer 3
101: luminescent layer
201: first organic layer
202: second organic layer
Detailed Description
The present specification will be described in more detail below. However, the following description relates to an embodiment of the present invention, and includes all the replaceable ranges within the equivalent range.
First, several terms in the present specification are clarified.
In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.
In the present specification, Cn means n carbon atoms.
In the present specification, Cn1-Cn2 means the number of carbon atoms is n1 to n 2.
In the present specification, examples of the substituent are described below, but not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium; a halogen group; a nitrile group; an alkyl group; a haloalkyl group; an alkoxy group; a haloalkoxy group; a cycloalkyl group; a silyl group; an alkenyl group; an amine group; an arylamine group; an aryl group; and 1 or 2 or more substituents of 1 or more heterocyclic groups containing N, O, S, Se and Si atom, or substituents formed by connecting 2 or more substituents of the above-exemplified substituents, or no substituent. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the connection of 2 or more substituents means that hydrogen of any one substituent is connected to other substituents. For example, isopropyl group may be bonded to phenyl group
A substituent of (1).
In the present specification, the connection of 3 substituents includes not only the connection of (substituent 1) - (substituent 2) - (substituent 3) continuously but also the connection of (substituent 2) and (substituent 3) to (substituent 1). For example, 2 phenyl groups and isopropyl groups are linked to form
A substituent of (1). The same explanation as above applies to the case where 4 or more substituents are bonded.
In this specification,. or
Indicates a site to which another substituent or a binding moiety binds.
In one embodiment of the present specification, "substituted or unsubstituted" means substituted with a substituent selected from deuterium, a halogen group; a nitrile group; C1-C20 alkyl; C1-C20 haloalkyl; alkoxy of C1-C20; haloalkoxy of C1-C20; cycloalkyl of C3-C20; silyl of C1-C50; alkenyl of C2-C20; an amine group; arylamine groups of C6-C50; aryl of C6-C30; and 1 or 2 or more substituents in a heterocyclic group of C2-C30 containing N, O, S, Se and 1 or more substituents among Si atoms, or a substituent formed by connecting 2 or more substituents, or no substituent.
In one embodiment of the present specification, "substituted or unsubstituted" means substituted with one substituent or 2 or more substituents selected from deuterium, an alkyl group having C1 to C10, an aryl group having C6 to C30, and a heterocyclic group having C2 to C30, or does not have any substituent.
In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30, 1 to 20, 1 to 10, or 1 to 5. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethylpropyl, 1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.
In the present specification, the haloalkyl group may be a straight chain or a branched chain, and means that hydrogen of the above alkyl group is substituted with 1 or 2 or more halogen groups. The number of carbon atoms is not particularly limited, but is preferably 1 to 30, 1 to 20, 1 to 10, or 1 to 5. The alkyl group can be used as described above for the alkyl group. Specific examples of the haloalkyl group include, but are not limited to, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, and the like.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, more preferably a cycloalkyl group having 3 to 30, 3 to 15, or 3 to 6 carbon atoms. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.
In the present specification, an alkoxy group is a group having an alkyl group bonded to an oxygen atom, and thus may be linear, branched, or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30, 1 to 20, 1 to 10, or 1 to 5. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy and the like, but is not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30, 2 to 20, 2 to 10, or 2 to 5. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.
In the present specification, the silyl group may be represented by the formula of — SiRaRbRc, and the above Ra, Rb and Rc may each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the amine group may be represented by the formula of-NRfRg, and the above Rf and Rg may each be hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. The amine group may be selected from the group consisting of an alkylamino group, an arylalkylamino group, an arylamino group, an arylheteroarylamino group, an alkylheteroarylamino group, and a heteroarylamino group, and more specifically, may be a dimethylamino group, a diphenylamino group, and the like, but is not limited thereto.
In the present specification, aryl means a 1-valent group of a 1-valent aromatic hydrocarbon or aromatic hydrocarbon derivative. In the present specification, an aromatic hydrocarbon refers to a compound containing a ring in which pi electrons are completely conjugated and which is planar, and a group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is fused to an aromatic hydrocarbon. In the present specification, an aryl group includes a 1-valent group in which 2 or more aromatic hydrocarbons or aromatic hydrocarbon derivatives are linked to each other. The aryl group is not particularly limited, but is preferably an aryl group having 6 to 50, 6 to 30, 6 to 25, 6 to 20, 6 to 18, or 6 to 13 carbon atoms, and the above aryl group may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto. Specifically, the polycyclic aromatic group includes naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, perylenyl, perylene,
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
In the present specification, when it is indicated that the fluorenyl group may be substituted, the substituted fluorenyl group includes all compounds in which substituents of five-membered rings of fluorene are spiro-bonded to each other to form an aromatic hydrocarbon ring. The substituted fluorenyl group includes, but is not limited to, 9 '-spirobifluorene, spiro [ cyclopentane-1, 9' -fluorene ], spiro [ benzo [ c ] fluorene-7, 9-fluorene ] and the like.
In the present specification, heteroaryl means an aromatic heterocycle having a valence of 1. Here, the aromatic heterocyclic ring refers to an aromatic ring or a 1-valent group of an aromatic ring derivative, and includes N, O, S or more of Si as a hetero atom in the ring. The aromatic ring derivative includes all structures in which an aromatic ring or an aliphatic ring is fused to an aromatic ring. In the present specification, the heteroaryl group includes a 1-valent group in which aromatic rings containing 2 or more heteroatoms or derivatives of aromatic rings containing heteroatoms are linked to each other. The number of carbon atoms of the above heteroaryl group is preferably 2 to 50, 2 to 30, 2 to 20, 2 to 18, or 2 to 13.
Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pteridinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, pyridoindolyl, indenopyrimidine (5H-indenopyrimidine), carbazolyl, benzoxazolyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pteridinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, pyridoindolyl, indenop
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, phenanthrolinyl, thiazolyl, isothiazolyl
Azolyl group,
And oxadiazolyl and thiadiazolyl groups, but are not limited thereto.
In the present specification, arylene means a group having two binding sites on an aryl group, i.e., a 2-valent group. The above description of aryl groups applies, except that they are each a 2-valent group.
In this specification, heteroarylene refers to a group having two binding sites on the heteroaryl group, i.e., a 2-valent group. The above description of heteroaryl groups applies, except that they are each a 2-valent group.
In the present specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest in steric structure to the substituent, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted at the ortho (ortho) position in the phenyl ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as groups "adjacent" to each other.
In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.
In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or aromatic and aliphatic fused ring, and may be selected from the cycloalkyl groups and the aryl groups described above, except that the hydrocarbon ring has a valence of 1. Examples of the aromatic and aliphatic condensed rings include, but are not limited to, 1,2,3, 4-tetrahydronaphthyl and 2, 3-dihydro-1H-indenyl.
In the present specification, the aromatic ring may be a monocyclic ring or a polycyclic ring, and may be selected from the above-mentioned illustrations of aryl groups, except that it is not 1-valent.
In the present specification, the heterocyclic ring contains 1 or more heteroatoms other than carbon atoms, specifically, the heteroatoms may contain 1 or more atoms selected from O, N, S, Si and the like. The heterocyclic ring may be monocyclic or polycyclic, may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from the heteroaryl groups described above except for having a valence of 1.
In chemical formulas 1 and 2 of the present specification, substitution by deuterium is included even in the case where a substituted substituent is not explicitly indicated.
Next, an organic light-emitting device and a compound including the same according to an embodiment of the present specification will be described.
The present specification provides an organic light emitting device, comprising: the organic light emitting device includes an anode, a cathode, and a first organic layer and a second organic layer between the anode and the cathode, wherein the first organic layer includes a compound represented by chemical formula 1, and the second organic layer includes a compound represented by chemical formula 2.
The compound represented by the above chemical formula 1 according to an embodiment includes boron (B) and 2 nitrogens in the center. Since the boron compound is introduced, the orbital overlap between HOMO (highest occupied molecular orbital) -LUMO (lowest unoccupied molecular orbital) is minimized, and thus a high triplet energy can be obtained while maintaining a wide band gap. Therefore, high efficiency of the device can be expected.
The compound represented by the above chemical formula 2 has a structure in which a heterocyclic ring including 1 or more N is connected to a spiro ring including O or S. Due to the above spiro ring containing O or S, steric hindrance is generated in the compound. The steric hindrance prevents crystallization during film formation, improves thermal stability, and enables stable layer formation even at high deposition temperatures. In one embodiment, when the compound represented by chemical formula 2 is used for the organic layer, the effect of improving the lifetime of the device may be expected due to high thermal stability and processability. Further, since the semiconductor device has a heterocyclic ring containing 1 or more N as a substituent, high efficiency of the device can be expected.
With respect to the compound represented by the above chemical formula 2, there is no symmetric structure (i.e., a structure in which R21 and R22, or R23 and R24 contain the structure of chemical formula 3 at the same time). That is, the structure of chemical formula 3 is asymmetrically included. At this time, dipole moment of the molecule is improved due to the asymmetric structure of chemical formula 2. Therefore, when the compound represented by chemical formula 2 is included in an organic layer (e.g., an electron transport layer) between the cathode and the light emitting layer, the electron injection rate into the light emitting layer is increased, so that the driving voltage of the organic light emitting device may be reduced. Further, the asymmetric structure reduces the crystallinity in a solution state, and thus an economical effect can be expected in terms of time and/or cost when forming an organic layer.
The value of the dipole moment of the compound represented by chemical formula 2 according to an embodiment of the present specification is 0.6 debye or more. The values of the dipole moments mentioned above can be attributed to structural features.
In this specification, dipole moment (dipole moment) as a physical quantity indicating the degree of polarity can be calculated by the following mathematical formula 1.
[ mathematical formula 1]
■ρ(r0): molecular Density (molecular Density)
■ V: volume (volume)
■ r: observation point (the point of observation)
■d3r0: per unit volume (an elementary volume me)
In the above mathematical formula 1, the value of the dipole moment can be obtained by calculating the Molecular density (Molecular density). For example, the molecular density can be obtained by obtaining the Charge (Charge) and Dipole (Dipole) of each atom by a method called herschifeld Charge Analysis (Hirshfeld Charge Analysis), and then calculating the molecular density according to the following formula.
■ρα(r-Rα): spherical average ground state atomic density
(spherically averaged ground-state atomic density)
■∑βρβ(r-Rβ): density of quasi-molecules (promollicula density)
■ ρ (r): molecular Density (molecular Density)
■ρα(r-Rα): at the coordinate RαDensity of free atoms alpha of
(density of the free atom α located at coordinates Rα)
q(α)＝-∫ρd(r)Wα(r)d3r
■Wα(r): weight function (weight function)
As described above, the compound of chemical formula 2 is an excellent material having an excellent electron injection effect due to the asymmetric structure. Therefore, it is preferable to maintain the hole-electron balance in the light-emitting layer. The LUMO energy of the compound represented by chemical formula 1 is high. When the compound of chemical formula 1 (i.e., small in absolute value) is used as a dopant of the light emitting layer, most of electrons transferred from the compound of chemical formula 2 are transferred to the host of the light emitting layer without being transferred to the compound of chemical formula 1, so that stability is improved. Therefore, the organic light emitting device including the compound of chemical formula 1 and the compound of chemical formula 2 is excellent in efficiency and lifespan.
In one embodiment of the present specification, X is B; p ═ O; or P ═ S.
In one embodiment of the present specification, X is B.
In one embodiment of the present specification, Z1 to Z3 are the same or different and each independently a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.
In one embodiment of the present specification, each of Z1 to Z3, which may be the same or different, is independently a substituted or unsubstituted C6 to C20 hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocyclic ring.
In one embodiment of the present specification, each of Z1 to Z3, which may be the same or different, is independently a substituted or unsubstituted monocyclic to tricyclic hydrocarbon ring or a substituted or unsubstituted monocyclic to tricyclic heterocyclic ring.
In one embodiment of the present specification, the Z1 to Z3 are the same as or different from each other, and each independently represents a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted carbazole ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, or a substituted or unsubstituted dibenzoselenophene ring.
In one embodiment of the present specification, the Z1 to Z3 are the same as or different from each other, and each independently represents a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted carbazole ring, a substituted or unsubstituted dibenzofuran ring, or a substituted or unsubstituted dibenzothiophene ring.
In one embodiment of the present specification, Z1 is a hydrocarbon ring substituted or unsubstituted with R1 or a heterocyclic ring substituted or unsubstituted with R1.
In one embodiment of the present specification, Z2 is a hydrocarbon ring substituted or unsubstituted with R2 or a heterocyclic ring substituted or unsubstituted with R2.
In one embodiment of the present specification, Z3 is a hydrocarbon ring substituted or unsubstituted with R3 or a heterocyclic ring substituted or unsubstituted with R3.
In one embodiment of the present specification, Z1 represents a benzene ring substituted or unsubstituted with R1, a naphthalene ring substituted or unsubstituted with R1, a carbazole ring substituted or unsubstituted with R1, a dibenzofuran ring substituted or unsubstituted with R1, or a dibenzothiophene ring substituted or unsubstituted with R1.
In one embodiment of the present specification, Z2 represents a benzene ring substituted or unsubstituted with R2, a naphthalene ring substituted or unsubstituted with R1, a carbazole ring substituted or unsubstituted with R2, a dibenzofuran ring substituted or unsubstituted with R2, or a dibenzothiophene ring substituted or unsubstituted with R2.
In one embodiment of the present specification, Z3 is a benzene ring substituted or unsubstituted with R3.
In one embodiment of the present specification, at least one of Z1 and Z2 is a substituted or unsubstituted aromatic hydrocarbon ring. Preferably a substituted or unsubstituted benzene ring.
In one embodiment of the present specification, Z1 is an aromatic hydrocarbon ring substituted or unsubstituted with R1, and Z2 is an aromatic hydrocarbon ring substituted or unsubstituted with R2.
In one embodiment of the present specification, Z1 is a hydrocarbon ring substituted or unsubstituted with R1, and Z2 is an aromatic heterocyclic ring substituted or unsubstituted with R2.
In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring.
In an embodiment of the present specification, the R1 to R3 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 haloalkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C1 to C30 silyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C1 to C10 amine group, a substituted or unsubstituted C6 to C60 arylamine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring.
In one embodiment of the present specification, R1 to R3 are the same or different and each independently represents one substituent or 2 or more substituents bonded to each other selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, an alkyl group having from C1 to C10, an alkoxy group having from C1 to C10, an amino group having from C1 to C10, an arylamino group having from C6 to C60, an aryl group having from C6 to C30, and a heterocyclic group having from C2 to C30.
In one embodiment of the present disclosure, R1 to R3, which are the same or different from each other, are each independently hydrogen, deuterium, an alkyl group having C1 to C10, an arylamine group having C6 to C60 substituted or unsubstituted with an alkyl group having C1 to C10 or an arylamine group having C6 to C60, an aryl group having C6 to C30, or a heterocyclic group having C2 to C30.
In one embodiment of the present specification, R1 to R3, which may be the same or different, are each independently hydrogen, deuterium, an alkyl group having C1 to C6, an arylamine group having C6 to C60, which is substituted or unsubstituted with an alkyl group having C1 to C10, an aryl group having C6 to C30, or a heterocyclic group having C2 to C30. In another embodiment, the heterocyclic group denoted by R1 to R3 is an N-containing heterocyclic group, and specifically may be a carbazolyl group.
In one embodiment of the present specification, R1 to R3 are the same or different and each independently a methyl group; an ethyl group; a tertiary butyl group; a phenyl group; a biphenyl group; diphenylamino substituted or unsubstituted with diphenylamino, ditolylamino or bis ((tert-butyl) phenyl) amino; or a carbazolyl group.
In one embodiment of the present specification, adjacent 2R 1 are bonded to each other to form a substituted or unsubstituted monocyclic or bicyclic aromatic hydrocarbon ring.
In one embodiment of the present specification, adjacent 2R 2 are bonded to each other to form a substituted or unsubstituted monocyclic or bicyclic aromatic hydrocarbon ring.
In one embodiment of the present specification, adjacent 2R 1 s combine with each other to form a benzene ring substituted with a C1-C10 alkyl group or unsubstituted.
In one embodiment of the present specification, adjacent 2R 2 s combine with each other to form a benzene ring substituted with a C1-C10 alkyl group or unsubstituted.
In one embodiment of the present specification, R3 represents one substituent or a substituent formed by connecting 2 or more substituents selected from the group consisting of hydrogen, deuterium, an alkyl group having C1 to C10, an arylamine group having C6 to C60, and a heterocyclic group having C2 to C30.
In one embodiment of the present specification, R3 represents hydrogen, deuterium, an alkyl group having 1 to 10, an arylamine group having 6 to 60 which may be substituted with an alkyl group having 1 to 10 or unsubstituted, or a heterocyclic group having 2 to 30.
In one embodiment of the present specification, R3 represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an arylamine group having 6 to 60 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, R3 represents hydrogen, deuterium, methyl, ethyl, tert-butyl, a diphenylamino group substituted or unsubstituted with tert-butyl, or a carbazolyl group.
In one embodiment of the present specification, R3 is hydrogen, deuterium, methyl, diphenylamino, or carbazolyl.
In one embodiment of the present specification, R1 and R2, which may be the same or different from each other, are each independently one substituent or 2 or more substituents linked together and selected from the group consisting of hydrogen, deuterium, an alkyl group having C1 to C10, an arylamine group having C6 to C60, an aryl group having C6 to C30, and a heterocyclic group having C2 to C30.
In one embodiment of the present disclosure, R1 and R2 are the same or different and each independently hydrogen, deuterium, an alkyl group having C1-C10, an arylamine group having C6-C60, which is substituted or unsubstituted with an alkyl group having C1-C10 or an arylamine group having C6-C60, an aryl group having C6-C30, or a heterocyclic group having C2-C30. In another embodiment, the heterocyclic group in R1 and R3 is an N-containing heterocyclic group, and specifically may be a carbazolyl group.
In one embodiment of the present specification, the R1 and R2 are the same or different from each other and each independently hydrogen, deuterium, or a C1-C10 alkyl group.
In one embodiment of the present specification, the R1 and R2 are the same or different from each other and each independently hydrogen, deuterium, or a C1-C6 alkyl group.
In one embodiment of the present specification, R1 and R2 are the same as or different from each other and each independently represents a methyl group; an ethyl group; a tertiary butyl group; a phenyl group; a biphenyl group; or a diphenylamino group which is unsubstituted or substituted by a diphenylamino group, a methyl group or a tert-butyl group.
In one embodiment of the present specification, R1 and R2 are the same or different and each independently a methyl group, an ethyl group, or a tert-butyl group.
In one embodiment of the present specification, a1 is N (R101) or O.
In one embodiment of the present specification, a2 is N (R102) or O.
In one embodiment of the present specification, a1 is N (R101).
In one embodiment of the present specification, a2 is N (R102).
In one embodiment of the present specification, a1 is O.
In one embodiment of the present specification, a2 is O.
In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
In one embodiment of the present specification, R101 and R102 are the same or different and each independently a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C6-C30 aryl group.
In one embodiment of the present specification, R101 and R102 are the same or different and each independently an alkyl group of C1 to C10, or an aryl group of C6 to C30 substituted or unsubstituted with an alkyl group of C1 to C10.
In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently represents a methyl group, a tert-butyl group, a phenyl group substituted or unsubstituted with a methyl group or a tert-butyl group, or a biphenyl group substituted or unsubstituted with a tert-butyl group.
In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following chemical formulae 101 to 108.
[ chemical formula 101]
[ chemical formula 102]
[ chemical formula 103]
[ chemical formula 104]
[ chemical formula 105]
[ chemical formula 106]
[ chemical formula 107]
[ chemical formula 108]
In the above-described chemical formulae 101 to 108,
x, A1 and A2 are as defined in chemical formula 1,
q is O, S, Se, N (R51) or C (R52) (R53),
r11 to R20 and R51 to R53, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring,
r11 and R12 are integers of 0 to 4, and when R11 and R12 are 2 or more, R11 and R12 may be the same as or different from each other,
r13 is an integer of 0 to 3, and when R13 is 2 or more, R13 are the same or different from each other,
r14 to R20 are integers of 0 to 6, and when R14 to R20 are 2 or more, R14 to R20 may be the same as or different from each other.
In one embodiment of the present specification, the definition of R1 may apply to R11. In another embodiment, the definitions of R2 may apply to R12, R14 to R20. In another embodiment, the definition of R3 may be applied to R13.
In one embodiment of the present specification, Q is O, S or N (R51).
In one embodiment of the present specification, Q is O or S.
In one embodiment of the present specification, R51 represents a substituted or unsubstituted aryl group having C6 to C30.
In one embodiment of the present specification, R51 is an aryl group having C6 to C20.
In one embodiment of the present specification, R51 is a phenyl group.
In one embodiment of the present specification, R52 and R53 are the same as or different from each other and each independently represents a methyl group or a phenyl group.
In one embodiment of the present specification, R11 to R20 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present disclosure, R11 to R20, which are the same or different from each other, are each independently hydrogen, deuterium, an alkyl group having C1 to C10, an arylamine group having C6 to C60 substituted or unsubstituted with an alkyl group having C1 to C10 or an arylamine group having C6 to C60, an aryl group having C6 to C30, or a heterocyclic group having C2 to C30.
In one embodiment of the present specification, R11 to R20, which may be the same or different, are each independently hydrogen, deuterium, an alkyl group having C1 to C6, an arylamine group having C6 to C60, which is substituted or unsubstituted with an alkyl group having C1 to C10, an aryl group having C6 to C30, or a heterocyclic group having C2 to C30. In another embodiment, the heterocyclic group denoted by R11 to R20 is an N-containing heterocyclic group, and specifically may be a carbazolyl group.
In one embodiment of the present specification, R11 to R20 are the same or different and each independently a methyl group; an ethyl group; a tertiary butyl group; a phenyl group; a biphenyl group; diphenylamino substituted or unsubstituted with diphenylamino, ditolylamino or bis ((tert-butyl) phenyl) amino; or a carbazolyl group.
In one embodiment of the present specification, R13 represents one substituent or a substituent formed by connecting 2 or more substituents selected from the group consisting of hydrogen, deuterium, an alkyl group having C1 to C10, an arylamine group having C6 to C60, and a heterocyclic group having C2 to C30.
In one embodiment of the present specification, R13 represents hydrogen, deuterium, an alkyl group having 1 to 10, an arylamine group having 6 to 60 which may be substituted with an alkyl group having 1 to 10 or unsubstituted, or a heterocyclic group having 2 to 30.
In one embodiment of the present specification, R13 represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an arylamine group having 6 to 60 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, R13 represents hydrogen, deuterium, methyl, ethyl, tert-butyl, a diphenylamino group substituted or unsubstituted with tert-butyl, or a carbazolyl group.
In one embodiment of the present specification, R13 is hydrogen, deuterium, methyl, diphenylamino, or carbazolyl.
In one embodiment of the present specification, R11, R12, and R14 to R20 are the same or different and each independently represents one substituent or 2 or more substituents bonded to each other selected from hydrogen, deuterium, an alkyl group having from C1 to C10, an arylamine group having from C6 to C60, an aryl group having from C6 to C30, and a heterocyclic group having from C2 to C30.
In one embodiment of the present disclosure, R11, R12, and R14 to R20 are the same or different and each independently represents hydrogen, deuterium, an alkyl group having from C1 to C10, an arylamine group having from C6 to C60, an aryl group having from C6 to C30, or a heterocyclic group having from C2 to C30, which is unsubstituted or substituted with an alkyl group having from C1 to C10 or an arylamine group having from C6 to C60. In another embodiment, the heterocyclic group of R11, R12, R14 to R20 is an N-containing heterocyclic group, and specifically may be a carbazolyl group.
In one embodiment of the present specification, R11, R12, and R14 to R20 are the same or different and each independently hydrogen, deuterium, or an alkyl group having from C1 to C10.
In one embodiment of the present specification, R11, R12, and R14 to R20 are the same or different and each independently hydrogen, deuterium, or an alkyl group having from C1 to C6.
In one embodiment of the present specification, R11, R12, and R14 to R20 are the same or different and each independently a methyl group; an ethyl group; a tertiary butyl group; a phenyl group; a biphenyl group; or a diphenylamino group which is unsubstituted or substituted by a diphenylamino group, a methyl group or a tert-butyl group.
In one embodiment of the present specification, R11, R12, and R14 to R20 are the same or different and each is independently a methyl group, an ethyl group, or a tert-butyl group.
In one embodiment of the present specification, the compound represented by the above chemical formula 1 is any one selected from the following compounds.
In one embodiment of the present specification, Y is O or S.
In one embodiment of the present specification, Y is O.
In one embodiment of the present specification, Y is S.
In one embodiment of the present specification, R21 to R24, which may be the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are represented by chemical formula 3, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted ring, and at least one of R21 to R24 is represented by chemical formula 3.
In one embodiment of the present specification, R21 is represented by chemical formula 3.
In one embodiment of the present specification, R22 is represented by chemical formula 3.
In one embodiment of the present specification, R23 is represented by chemical formula 3.
In one embodiment of the present specification, R24 is represented by chemical formula 3.
In one embodiment of the present specification, R21 to R24, which may be the same or different, are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 heterocyclic group, or are represented by the above chemical formula 3, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted C3 to C30 ring.
In one embodiment of the present specification, the R21 to R24, which may be the same or different, are each independently hydrogen, deuterium, an alkyl group having C1 to C10, an aryl group having C6 to C30, which is unsubstituted or substituted with an alkyl group having C1 to C10, or represented by the above chemical formula 3, or adjacent substituents are bonded to each other to form a benzene ring.
In one embodiment of the present specification, R21 to R24, which may be the same or different, are each independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl substituted or unsubstituted with methyl or tert-butyl, biphenyl, or naphthyl, or are represented by chemical formula 3, or adjacent substituents are bonded to each other to form a benzene ring.
In one embodiment of the present specification, at least one of R21 to R24 is represented by the chemical formula 3, and the others are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 heterocyclic group, or 2 of adjacent R21, 2 of adjacent R22, 2 of adjacent R23, or 2 of adjacent R24 are bonded to each other to form a substituted or unsubstituted C3 to C30 ring.
In one embodiment of the present specification, one or two of R21 to R24 are represented by the above chemical formula 3, and the others are the same as or different from each other, and each independently represents hydrogen, deuterium, an alkyl group of C1 to C10, or an aryl group of C6 to C30 which is substituted or unsubstituted with an alkyl group of C1 to C10, or 2 of adjacent R21, 2 of adjacent R22, 2 of adjacent R23, or 2 of adjacent R24 are bonded to each other to form a benzene ring.
In one embodiment of the present specification, one or two of R21 to R24 are represented by the chemical formula 3, and the others are the same or different from each other, and each independently represents hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl substituted or unsubstituted with methyl or tert-butyl, biphenyl, or naphthyl, or 2 of adjacent R21, 2 of adjacent R22, 2 of adjacent R23, or 2 of adjacent R24 are bonded to each other to form a benzene ring.
In one embodiment of the present specification, one or two of R21 to R24 are represented by the chemical formula 3, and the others are the same or different from each other, and each independently represents hydrogen, deuterium, or a phenyl group substituted with a methyl group or unsubstituted, or 2 of adjacent R21 or 2 of adjacent R22 are bonded to each other to form a benzene ring.
In one embodiment of the present specification, adjacent 2 of the above R21 are bonded to each other to form a substituted or unsubstituted benzene ring.
In one embodiment of the present specification, adjacent 2 of the above R22 are bonded to each other to form a substituted or unsubstituted benzene ring.
In one embodiment of the present specification, 2 adjacent R21 are bonded to each other to form a benzene ring.
In one embodiment of the present specification, 2 adjacent R22 are bonded to each other to form a benzene ring.
In one embodiment of the present specification, R21 to R24 are the same or different and each independently an integer of 0 to 4, R21 is 2 or more, R21 is the same or different, R22 is 2 or more, R22 is the same or different, R23 is 2 or more, R23 is the same or different, and R24 is 2 or more, R24 is the same or different.
In one embodiment of the present disclosure, r21 to r24 are the same or different and each independently 0 to 2.
In one embodiment of the present specification, X1 is N or C (R31).
In one embodiment of the present specification, X2 is N or C (R32).
In one embodiment of the present specification, X3 is N or C (R33).
In one embodiment of the present disclosure, one or more of X1 to X3 is N.
In one embodiment of the present disclosure, 2 or more of X1 to X3 are N.
In one embodiment of the present disclosure, each of X1 to X3 is N.
In one embodiment of the present specification, X1 is N, X2 is N, and X3 is C (R33). In another embodiment, R33 combines with Ar2 to form a benzene ring.
In one embodiment of the present specification, X1 is N, X2 is C (R32), and X3 is N. In another embodiment, R33 combines with Ar2 to form a benzene ring.
In one embodiment of the present specification, R31, R32, and R33 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or forms a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring in combination with Ar1 or Ar 2.
In one embodiment of the present specification, R31, R32, and R33 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted aryl group having C6 to C30, or a substituted or unsubstituted heterocyclic group having C2 to C30, or an aromatic hydrocarbon ring having C6 to C30 which is substituted or unsubstituted or a heterocyclic ring having C2 to C30 which is substituted or unsubstituted, in combination with Ar1 or Ar 2. In another embodiment, "substituted or unsubstituted" means substituted with one substituent or 2 or more substituents selected from deuterium, an alkyl group of C1-C10, an aryl group of C6-C30, and a heteroaryl group of C2-C30, or without any substituent.
In one embodiment of the present specification, R31, R32, and R33 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted monocyclic to tetracyclic aryl group, or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group, or combines with Ar1 or Ar2 to form a substituted or unsubstituted monocyclic to tetracyclic aromatic hydrocarbon ring, or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic ring. In another embodiment, "substituted or unsubstituted" means substituted with one substituent or 2 or more substituents selected from deuterium, an alkyl group of C1-C10, an aryl group of C6-C30, and a heteroaryl group of C2-C30, or without any substituent.
In one embodiment of the present specification, R31, R32, and R33 are the same or different from each other, and each independently represents hydrogen, deuterium, phenyl, biphenyl, naphthyl, carbazolyl, phenylcarbazolyl, or benzocarbazolyl, or is combined with Ar1 or Ar2 to form a benzene ring substituted or unsubstituted with an aryl group of C6 to C30 or a heterocyclic group of C2 to C30.
In one embodiment of the present specification, each of R31, R32, and R33 is hydrogen or deuterium.
In one embodiment of the present specification, R31, R32 and R33 are each hydrogen.
In one embodiment of the specification, R31 is bonded to Ar1 to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In one embodiment of the present specification, R32 is bonded to Ar1 to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In one embodiment of the present specification, R32 is bonded to Ar2 to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In one embodiment of the present specification, R33 is bonded to Ar2 to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In one embodiment of the present specification, R31 described above is bonded to Ar1 to form a benzene ring substituted or unsubstituted with R41.
In one embodiment of the present specification, R32 described above is bonded to Ar1 to form a benzene ring substituted or unsubstituted with R41.
In one embodiment of the present specification, R32 described above is bonded to Ar2 to form a benzene ring substituted or unsubstituted with R41.
In one embodiment of the present specification, R33 described above is bonded to Ar2 to form a benzene ring substituted or unsubstituted with R41.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, or forms a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring in combination with R31, R32, or R33.
In one embodiment of the present specification, Ar1 and Ar2, which are the same or different from each other, are each independently a C6-C30 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, a C1-C10 alkyl group, a C6-C30 aryl group, and a C2-C20 heterocyclic group, the substituents being 2 or more substituents selected from the above group; or a heterocyclic group of C6-C30 which is unsubstituted or substituted by one or more substituents selected from the group consisting of deuterium, a cyano group, an alkyl group of C1-C10, an aryl group of C6-C30 and a heterocyclic group of C2-C20.
In one embodiment of the present specification, Ar1 and Ar2, which are the same as or different from each other, are each independently an aryl group of C6 to C30, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, an aryl group of C6 to C30, and a heterocyclic group of C2 to C20, wherein the substituents are 2 or more substituents selected from the group; or a C6-C30 heterocyclic group which is unsubstituted or substituted by one substituent selected from the group consisting of deuterium, an aryl group having C6-C30, and a heterocyclic group having C2-C20, or by 2 or more substituents selected from the above-mentioned group.
In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and each independently represents an aryl group of C6 to C20 which is unsubstituted or substituted with one substituent selected from the group consisting of deuterium, a cyano group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, and a carbazolyl group, or with 2 or more substituents selected from the group.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group substituted or unsubstituted with R41, or a heterocyclic group substituted or unsubstituted with R42, or forms an aromatic hydrocarbon ring substituted or unsubstituted with R41, or a heterocyclic ring substituted or unsubstituted with R42 in combination with R31, R32, or R33.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group of C6 to C30 substituted or unsubstituted with R41, a heterocyclic group of C2 to C30 substituted or unsubstituted with R42, or an aromatic hydrocarbon ring of C6 to C30 substituted or unsubstituted with R41 or a heterocyclic ring of C2 to C30 substituted or unsubstituted with R42 in combination with R31, R32, or R33.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group of C6 to C20 substituted or unsubstituted with R41, a heterocyclic group of C2 to C20 substituted or unsubstituted with R42, or an aromatic hydrocarbon ring of C6 to C20 substituted or unsubstituted with R41 or a heterocyclic ring of C2 to C20 substituted or unsubstituted with R42 in combination with R31, R32, or R33.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic to pentacyclic aryl group substituted or unsubstituted with R41, or a monocyclic to pentacyclic heterocyclic group substituted or unsubstituted with R42, or forms a monocyclic to pentacyclic aromatic hydrocarbon ring substituted or unsubstituted with R41 in combination with R31, R32, or R33; or a monocyclic to pentacyclic heterocycle optionally substituted with R42.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic to tetracyclic aryl group substituted or unsubstituted with R41, or a monocyclic to tetracyclic heterocyclic group substituted or unsubstituted with R42, or forms a monocyclic to tetracyclic aromatic hydrocarbon ring substituted or unsubstituted with R41 in combination with R31, R32, or R33; or a monocyclic to tetracyclic heterocycle substituted or unsubstituted with R42.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic to tricyclic aryl group substituted or unsubstituted with R41, a monocyclic to tricyclic heterocyclic group substituted or unsubstituted with R42, or a monocyclic to tricyclic aromatic hydrocarbon ring substituted or unsubstituted with R41 in combination with R31, R32, or R33; or a monocyclic to tricyclic heterocycle substituted or unsubstituted with R42.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a fluoranthenyl group, a phenalenyl group, an anthracenyl group, a fluorenyl group, or a dimethylfluorenyl group, and the substituent is substituted or unsubstituted with R41.
In one embodiment of the present specification, Ar1 and Ar2, which are the same or different from each other, are each independently a monocyclic to five-membered heterocyclic group containing N, O, S or Si, which is substituted or unsubstituted with R42.
In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a carbazolyl group, a phenylcarbazolyl group, a benzocarbazolyl group, an indenocarbazolyl group, a dibenzothienyl group, a dibenzofuran group, a dibenzothiaole group (dibenzosilole), a thiophene group
An oxazinyl, phenothiazinyl, phenazinyl, acridinyl, dihydrophenazinyl, dihydroacridinyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrimidoindolyl or pyridoindolyl group, said substituent being substituted or unsubstituted by R42.
In one embodiment of the present specification, Ar1 is bonded to R31 to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In one embodiment of the present specification, Ar1 is bonded to R32 to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In one embodiment of the present specification, Ar2 is bonded to R32 to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In one embodiment of the present specification, Ar2 is bonded to R33 to form a substituted or unsubstituted ring, a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In one embodiment of the present specification, Ar1 is bonded to R31 to form a benzene ring substituted or unsubstituted with R41.
In one embodiment of the present specification, Ar1 is bonded to R32 to form a benzene ring substituted or unsubstituted with R41.
In one embodiment of the present specification, Ar2 is bonded to R32 to form a benzene ring substituted or unsubstituted with R41.
In one embodiment of the present specification, Ar2 is bonded to R33 to form a benzene ring substituted or unsubstituted with R41.
In one embodiment of the present specification, R41 and R42 are the same or different and each independently one selected from deuterium, a halogen group, a nitrile group, an alkyl group, a halogenated alkyl group, an alkoxy group, a silyl group, an aryl group, and a heterocyclic group, or a group in which 2 or more substituents are bonded.
In one embodiment of the present specification, R41 and R42, which may be the same or different from each other, are each independently one selected from deuterium, a halogen group, a nitrile group, an alkyl group having from C1 to C20, a halogenated alkyl group having from C1 to C20, an alkoxy group having from C1 to C20, a silyl group having from C1 to C50, an aryl group having from C6 to C50, and a heterocyclic group having from C2 to C50, or a group in which 2 or more substituents are bonded to each other.
In one embodiment of the present specification, R41 and R42, which may be the same or different from each other, are each independently one selected from deuterium, a halogen group, a nitrile group, an alkyl group having from C1 to C10, a halogenated alkyl group having from C1 to C10, an alkoxy group having from C1 to C10, a silyl group having from C1 to C30, an aryl group having from C6 to C30, and a heterocyclic group having from C2 to C30, or a group in which 2 or more substituents are bonded to each other.
In one embodiment of the present specification, R41 and R42, which may be the same or different from each other, are each independently one selected from deuterium, a halogen group, a nitrile group, an alkyl group having from C1 to C5, a halogenated alkyl group having from C1 to C5, an alkoxy group having from C1 to C5, a silyl group having from C1 to C20, an aryl group having from C6 to C20, and a heterocyclic group having from C2 to C20, or a group in which 2 or more substituents are bonded to each other.
In one embodiment of the present specification, R41 and R42 are the same or different and each independently one selected from deuterium, a halogen group, a nitrile group, an alkyl group having from C1 to C20, a haloalkyl group having from C1 to C20, an alkoxy group having from C1 to C20, a silyl group having from C1 to C50, a monocyclic to pentacyclic aryl group, and a monocyclic to pentacyclic heterocyclic group, or a group in which 2 or more substituents are bonded to each other.
In one embodiment of the present specification, R41 and R42, which are the same or different from each other, are each independently one selected from deuterium, a halogen group, a nitrile group, an alkyl group having from C1 to C10, a haloalkyl group having from C1 to C10, an alkoxy group having from C1 to C10, a silyl group having from C1 to C30, a monocyclic to tetracyclic aryl group, and a monocyclic to tetracyclic heterocyclic group, or a group in which 2 or more substituents are bonded to each other.
In one embodiment of the present specification, R41 and R42 are the same or different and each independently one selected from deuterium, a halogen group, a nitrile group, an alkyl group having from C1 to C5, a haloalkyl group having from C1 to C5, an alkoxy group having from C1 to C5, a silyl group having from C1 to C20, a monocyclic to tricyclic aryl group, and a monocyclic to tricyclic heterocyclic group, or a group in which 2 or more substituents are bonded to each other.
In one embodiment of the present specification, R41 and R42, which are the same or different from each other, are each independently selected from deuterium, a nitrile group, methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, trimethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluoranthenyl, phenalenyl, anthracenyl, fluorenyl, dimethylfluorenyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, indenocarbazolyl, dibenzothienyl, dibenzofuranyl, dibenzopyrrolyl (dibenzosilole), thiophene
One of an oxazinyl group, a phenothiazinyl group, a phenazinyl group, an acridinyl group, a dihydrophenazinyl group, a dihydroacridinyl group, a pyridyl group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrimidoindolyl group, and a pyridoindolyl group, or a group in which 2 or more substituents are linked.
In one embodiment of the present specification, L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group.
In one embodiment of the present specification, L is a direct bond, a substituted or unsubstituted arylene group having C6 to C30, or a substituted or unsubstituted heterocyclic group having 2 valences of C2 to C30.
In one embodiment of the present specification, L is a direct bond, an arylene group having from C6 to C30, or a heterocyclic group having a valence of 2 from C2 to C30. The arylene group or the 2-valent heterocyclic group may be substituted or unsubstituted with a substituent formed by connecting one or 2 or more substituents selected from the group consisting of a nitrile group, an alkyl group having 1 to 10, an aryl group having 6 to 30 and a heterocyclic group having 2 to 30.
In one embodiment of the present specification, L is a direct bond, a monocyclic to pentacyclic arylene group, or a monocyclic to pentacyclic 2-valent heterocyclic group. The arylene group or the 2-valent heterocyclic group may be substituted or unsubstituted with a substituent formed by connecting one or 2 or more substituents selected from the group consisting of a nitrile group, an alkyl group having 1 to 10, an aryl group having 6 to 30 and a heterocyclic group having 2 to 30.
In one embodiment of the present specification, L is a direct bond, a monocyclic to tetracyclic arylene group, or a monocyclic to tetracyclic 2-valent heterocyclic group. The arylene or 2-valent heterocyclic group is selected from nitrile group, C1-C10 alkyl group, C6-C30 aryl group; and a substituent formed by connecting one substituent or 2 or more substituents in the heterocyclic group of C2-C30.
In one embodiment of the present specification, L is a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthracenylene group, a phenanthrenyl group having a valence of 2, a triphenylene group having a valence of 2, a fluoranthenyl group having a valence of 2, a phenalene group having a valence of 2, a fluorenyl group having a valence of 2, a dimethylfluorenyl group having a valence of 2, a carbazolyl group having a valence of 2, a phenylcarbazolyl group having a valence of 2, a benzocarbazolyl group having a valence of 2, an indenocarbazolyl group having a valence of 2, a dibenzothienyl group having a valence of 2, a dibenzofuranyl group having a valence of 2, and a thiophen group having a valence of 2
An oxazinyl group, a 2-valent phenothiazinyl group, a 2-valent phenazinyl group, a 2-valent acridinyl group, a 2-valent dihydrophenazinyl group, a 2-valent dihydroacridinyl group, a 2-valent pyridyl group, a 2-valent pyrimidinyl group, a 2-valent quinolyl group, a 2-valent isoquinolyl group, a 2-valent quinazolinyl group, a 2-valent pyridopyrimidinyl group, a 2-valent pyridopyrazinyl group, a 2-valent pyrimidoindolyl group, or a 2-valent pyridoindolyl group. The above-mentioned linking group (L) is selected from the group consisting of a nitrile group, an alkyl group having from C1 to C10, an aryl group having from C6 to C30, and a heterocyclic group having from C2 to C30Or a substituent in which 2 or more substituents are linked may be substituted or unsubstituted.
In one embodiment of the present specification, L is a direct bond, an arylene group having from C6 to C30, or a heterocyclic group having a valence of 2 from C2 to C30.
In one embodiment of the present specification, L is a direct bond, an arylene group having from C6 to C30, or a 2-valent N-containing heterocyclic group having from C2 to C30.
In one embodiment of the present specification, L is a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a 2-valent dibenzothienyl group, a 2-valent dibenzofuranyl group, a 2-valent pyridyl group, a 2-valent pyrimidyl group, a 2-valent quinolyl group, or a 2-valent isoquinolyl group.
In one embodiment of the present specification, L is a direct bond, a phenylene group, a 2-valent pyridyl group, or a 2-valent dibenzothienyl group.
In one embodiment of the present specification, L is a direct bond, phenylene, biphenylene, or naphthylene.
In one embodiment of the present specification, L is a direct bond.
In one embodiment of the present specification, m is an integer of 0 to 2.
In one embodiment of the present specification, m is 0 or 1.
In one embodiment of the present specification, m is 0.
In one embodiment of the present specification, r21 is an integer of 0 to 2.
In one embodiment of the present specification, r22 is an integer of 0 to 2.
In one embodiment of the present specification, r23 is an integer of 0 to 2.
In one embodiment of the present specification, r24 is an integer of 0 to 2.
In one embodiment of the present specification, r21 is 1.
In one embodiment of the present specification, r22 is 1.
In one embodiment of the present specification, r23 is 1.
In one embodiment of the present specification, r24 is 1.
In one embodiment of the present specification, the chemical formula 3 is represented by any one of the following chemical formulae 301 to 303.
[ chemical formula 301]
[ chemical formula 302]
[ chemical formula 303]
In the above-described chemical formulae 301 to 303,
l, m, Ar1 and Ar2 are as defined in chemical formula 3,
more than one of X1 to X3 is N, and the rest is CH or CD,
r30 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
r30 is an integer of 0 to 4, and when R30 is 2 or more, R30 may be the same as or different from each other.
In one embodiment of the present specification, in chemical formula 301, X1 is N or C (R31), X2 is N or C (R32), X3 is N or C (R33), one or more of X1 to X3 are N, and R31, R32, and R33, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, in the chemical formula 301, R31, R32, and R33 are hydrogen.
In one embodiment of the present specification, R30 represents hydrogen, deuterium, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group.
In one embodiment of the present specification, R30 is hydrogen, methyl, phenyl or benzocarbazolyl.
In one embodiment of the present specification, R30 is hydrogen.
In one embodiment of the present specification, the chemical formula 2 is represented by any one of chemical formulas 201 to 204 below.
[ chemical formula 201]
[ chemical formula 202]
[ chemical formula 203]
[ chemical formula 204]
In the above-described chemical formulas 201 to 204,
x1 to X3, L, m, Ar1, Ar2, R21 to R24, R21 to R24 and Y are as defined in chemical formula 2,
x4 is N or C (R34), X5 is N or C (R35), X6 is N or C (R36), at least one of X4 to X6 is N,
r34, R35 and R36 are the same as or different from each other, and each independently is hydrogen or deuterium, or combines with Ar3 or Ar4 to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring,
ar3 and Ar4 are the same as or different from each other, and each independently represents an aryl group substituted or unsubstituted with R43, or a heterocyclic group substituted or unsubstituted with R44, or combined with R34, R35, or R36 to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,
r43 and R44, which may be the same or different from each other, are each independently one member selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a halogenated alkyl group, an alkoxy group, a silyl group, an aryl group and a heterocyclic group, or a group in which 2 or more substituents are bonded to each other,
l11 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,
m11 is an integer of 0 to 4, and when m11 is 2 or more, L11 are the same as or different from each other.
In one embodiment of the present specification, the chemical formulas 201 to 204
May be represented by any one of the above chemical formulas 301 to 303.
In one embodiment of the present specification, the above description of L may be applied to L11.
In one embodiment of the present specification, the above description of m can be applied to m 11.
In one embodiment of the present disclosure, the descriptions of X1 to X3 may be applied to the above-mentioned X4 to X6.
In one embodiment of the present specification, the descriptions of Ar1 and Ar2 may be applied to Ar3 and Ar 4.
According to an embodiment of the present disclosure, the chemical formula 2 is represented by any one of the following chemical formulas 211 to 218.
[ chemical formula 211]
[ chemical formula 212]
[ chemical formula 213]
[ chemical formula 214]
[ chemical formula 215]
[ chemical formula 216]
[ chemical formula 217]
[ chemical formula 218]
In the above-described chemical formulas 211 to 218,
x1 to X3, L, m, Ar1, Ar2, R21 to R24, R21 to R24 and Y are as defined in chemical formula 2.
According to an embodiment of the present specification, the chemical formula 2 is represented by any one of the following chemical formulae 401 to 403.
[ chemical formula 401]
[ chemical formula 402]
[ chemical formula 403]
In the above-described chemical formulae 401 to 403,
x1 to X3, L, m, Ar1, Ar2, R21, R22, R24, R21, R22, R24 and Y are as defined in chemical formula 2,
r25 and R26, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
r25 and R26 are the same as or different from each other and each independently an integer of 0 to 6, and when R25 is 2 or more, R25 are the same as or different from each other, and when R26 is 2 or more, R26 are the same as or different from each other.
In one embodiment of the present specification, the above description about R21 and R22 may be applied to R25 and R26.
According to an embodiment of the present specification, the compound represented by the above chemical formula 2 is any one selected from the following compounds.
The present specification provides an organic light emitting device, comprising: the organic light emitting device includes an anode, a cathode, and a first organic layer and a second organic layer between the anode and the cathode, wherein the first organic layer includes a compound represented by chemical formula 1, and the second organic layer includes a compound represented by chemical formula 2.
The organic light emitting device according to the present specification may include additional organic layers in addition to the first and second organic layers described above.
In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the other member but also a case where the other member exists between the two members.
In the present specification, the above-mentioned "layer" is used interchangeably with "film" mainly used in the art, and means a coating layer covering a target area. The size of the above "layer" is not limited, and the size of each "layer" may be the same or different. In an embodiment, the size of the "layer" may be equal to the entire device, may correspond to the size of the specific functional area, or may be as small as a sub-pixel (sub-pixel).
In the present specification, the meaning that a specific substance a is contained in a B layer is that i) the case where 1 or more substances a are contained in a B layer of one layer, and ii) the case where a B layer is composed of 1 or more layers and substances a are contained in 1 or more layers of a plurality of B layers are all included.
In the present specification, the meaning that the specific substance a is contained in the C layer or the D layer includes i) contained in 1 or more of the 1 or more C layers, ii) contained in 1 or more of the 1 or more D layers, or iii) contained in the 1 or more C layers and the 1 or more D layers, respectively.
The organic layer of the organic light-emitting device in the present specification may have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, the organic el device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, or the like. However, the structure of the organic light emitting device is not limited thereto, and a greater or lesser number of organic layers may be included.
In one embodiment of the present specification, the compound represented by the above chemical formula 1 is contained in the first organic layer.
In one embodiment of the present specification, the first organic layer includes a hole injection layer, a hole transport layer, a hole control layer, an electron blocking layer, a layer which simultaneously performs hole transport and injection, or a light emitting layer.
In one embodiment of the present disclosure, the first organic layer is a light-emitting layer.
In one embodiment of the present specification, the light emitting layer includes a compound represented by the chemical formula 1 as a dopant of the light emitting layer.
In one embodiment of the present specification, the compound represented by the above chemical formula 1 is included by 0.01 parts by weight or more and less than 20 parts by weight with respect to 100 parts by weight of the total weight of the first organic layer. More preferably, the organic material layer contains 1 part by weight or more and 10 parts by weight or less with respect to 100 parts by weight of the total weight of the first organic material layer.
In one embodiment of the present disclosure, the light emitting layer includes the compound represented by chemical formula 1, and the light emitting layer including the compound represented by chemical formula 1 is blue.
In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound as a dopant of the light-emitting layer and may further include a host.
In one embodiment of the present specification, the first organic layer is a light-emitting layer and includes an anthracene derivative in addition to the compound represented by chemical formula 1. Specifically, the compound described above is contained as a dopant of the light-emitting layer, and the anthracene derivative is contained as a host of the light-emitting layer.
In one embodiment of the present specification, the anthracene derivative is a compound represented by the following chemical formula H01 or H02,
[ chemical formula H01]
[ chemical formula H02]
In the above chemical formulae H01 and H02,
d is deuterium, k1 is an integer from 0 to 8, k2 is an integer from 0 to 7,
l21 to L23, which are identical to or different from one another, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
ar21 to Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
In one embodiment of the present specification, L21 to L23, which are the same or different from each other, are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group containing N, O or S having 2 to 30 carbon atoms.
In one embodiment of the present specification, L21 to L23, which are the same or different from each other, are each independently a direct bond, phenylene, biphenylene, or naphthylene, and L21 to L23 may each contain 1 or more deuterium.
In one embodiment of the present specification, Ar21 to Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
In one embodiment of the present specification, Ar21 to Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
In one embodiment of the present disclosure, Ar21 to Ar23, which are the same or different from each other, are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a dibenzothiophenyl group, or a naphthobenzothiophenyl group, and Ar21 to Ar23 may each include 1 or more deuterium.
In one embodiment of the present specification, Ar21 and Ar22 are different from each other.
In one embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group and Ar22 is a substituted or unsubstituted aryl group.
In one embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl and Ar22 is a substituted or unsubstituted heteroaryl.
In one embodiment of the present specification, Ar21 is an aryl group substituted or unsubstituted with deuterium, and Ar22 is an aryl group substituted or unsubstituted with deuterium.
In one embodiment of the present specification, Ar21 is aryl substituted or unsubstituted with deuterium, and Ar22 is heteroaryl substituted or unsubstituted with deuterium.
In one embodiment of the present specification, Ar23 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, Ar23 is an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present specification, Ar23 is phenyl, biphenyl, terphenyl, naphthyl, or phenanthryl.
In one embodiment of the present specification, the anthracene derivative is selected from any one of the following compounds.
The compound represented by the above chemical formula H may include 1 species or 2 or more species in the organic layer (specifically, the light-emitting layer). Specifically, the first host represented by the above chemical formula H and the second host represented by the above chemical formula H may be included in the organic layer.
The weight ratio of the first body represented by the above chemical formula H to the second body represented by the above chemical formula H is 95:5 to 5:95, and more preferably 30:70 to 70: 30.
In another embodiment, the first body and the second body are different from each other.
In another embodiment, Ar21 and Ar22 of the first body represented by formula H above, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group; ar21 of the second body represented by the above formula H is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heteroaryl group.
In one embodiment of the present specification, the organic light emitting device includes 1 or more light emitting layers in addition to the light emitting layer including the compound represented by chemical formula 1. The 1 or more light-emitting layers may each contain the fluorescent dopant or the phosphorescent dopant.
According to one embodiment of the present disclosure, the organic light emitting device includes 2 or more light emitting layers, one of the 2 or more light emitting layers includes a fluorescent dopant, and the other layer includes a phosphorescent dopant.
According to one embodiment of the present invention, the light emitting device includes a light emitting layer including the compound represented by the chemical formula 1, and the maximum light emission peak of the light emitting layer is 400nm to 500 nm.
In one embodiment of the present specification, the organic light-emitting device includes 2 or more light-emitting layers.
In one embodiment of the present specification, the maximum light emission peaks of the respective light-emitting layers are different from each other. Specifically, the organic light emitting device further includes 1 or more light emitting layers that exhibit a maximum light emission peak in a wavelength range different from a wavelength range in which the maximum light emission peak of the light emitting layer including 1 or more compounds represented by the above chemical formula 1 is exhibited.
The maximum light emission peak of the light emitting layer including the compound represented by the above chemical formula 1 may be 400nm to 500nm, and the maximum light emission peak of the other light emitting layer may show a maximum light emission peak of 510nm to 580nm, or 610nm680 nm.
In one embodiment of the present specification, a light emitting layer other than the light emitting layer including 1 or more compounds represented by the above chemical formula 1 includes a phosphorescent dopant. Specifically, the light-emitting layer of 1 or more layers that exhibits the maximum emission peak in a wavelength range different from the wavelength range in which the maximum emission peak of the light-emitting layer including 1 or more compounds represented by the above chemical formula 1 is exhibited contains a phosphorescent dopant.
In one embodiment of the present description, one light emitting layer is blue, and the other light emitting layer may include a blue, red, or green light emitting compound known in the art.
According to an embodiment of the present invention, the organic light emitting device includes 2 or more light emitting layers, one light emitting layer includes a fluorescent dopant, and the other light emitting layer includes a phosphorescent dopant.
In the case where the organic light-emitting device of the present invention includes 2 or more light-emitting layers, the 2 or more light-emitting layers may be stacked in order in the vertical direction or may be stacked in parallel in the horizontal direction.
In one embodiment of the present specification, the organic light-emitting device includes 3 or more light-emitting layers. In one embodiment, the 3 or more light emitting layers are stacked in this order, and the 3 or more light emitting layers may each exhibit a maximum light emission peak in the same wavelength range. In this case, the maximum emission peak is in the blue region of 400nm to 500 nm.
In one embodiment of the present specification, the compound represented by the above chemical formula 2 is contained in the second organic layer.
In one embodiment of the present specification, the compound represented by the above chemical formula 2 is contained in a hole blocking layer, an electron adjusting layer, an electron transporting layer, an electron injecting layer, or a layer that simultaneously transports and injects electrons.
In one embodiment of the present disclosure, the second organic layer is included in a hole blocking layer, an electron adjusting layer, an electron transporting layer, an electron injecting layer, or a layer which transports and injects electrons at the same time.
In one embodiment of the present disclosure, the second organic layer includes an electron transport layer or a layer which transports and injects electrons simultaneously.
In one embodiment of the present specification, the first organic layer and the second organic layer are provided in contact with each other.
In one embodiment of the present specification, a first organic material layer is provided between the anode and the cathode. In another embodiment, the second organic layer is provided between the first organic layer and the cathode.
In one embodiment of the present specification, the second organic layer is provided in contact with a cathode.
In one embodiment of the present disclosure, an electron transport region is further included between the second organic layer and the first organic layer.
In one embodiment of the present specification, the second organic layer is provided in contact with the light-emitting layer. Specifically, the light-emitting layer is provided in contact with the surface of the cathode facing the light-emitting layer.
In one embodiment of the present specification, the second organic layer further includes 1 or 2 or more n-type dopants selected from alkali metals and alkaline earth metals, in addition to the compound represented by chemical formula 2.
When the organic alkali metal compound or the organic alkaline earth metal compound is used as the n-type dopant, stability of holes in the light emitting layer can be secured, so that the life of the organic light emitting device can be improved. In addition, the electron mobility of the electron transport layer and the proportion of the organic alkali metal compound or the organic alkaline earth metal compound are adjusted to maximize the balance of holes and electrons in the light emitting layer, and thus the light emitting efficiency can be increased.
In this specification, LiQ is more preferable as the n-type dopant used for the second organic layer. The second organic layer may include the heterocyclic compound of chemical formula 2 and the n-type dopant at a weight ratio of 1:9 to 9: 1. Preferably, the heterocyclic compound of the above chemical formula 1 and the above n-type dopant may be contained at 2:8 to 8:2, and more preferably, may be contained at 3:7 to 7: 3.
In one embodiment of the present description, the cathode is a multilayer structure of a metal or a metal alloy.
In one embodiment, an organic light emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode. In another embodiment, the first electrode is a cathode and the second electrode is an anode.
In one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device of a normal structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.
In one embodiment of the present specification, the organic light emitting device may be an inverted (inverted) type organic light emitting device in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.
Fig. 1 to 4 illustrate a stacked structure of an organic light emitting device of the present invention.
Fig. 1 shows an organic light emitting device in which a substrate 0, a cathode 1, a second organic layer 202, a first organic layer 201, and an anode 4 are sequentially stacked in a vertical direction. In one embodiment of the present specification, the compound represented by the above chemical formula 1 is contained in the first organic layer 201, and the compound represented by the above chemical formula 2 is contained in the second organic layer 202.
Fig. 2 to 4 are laminated structures showing the organic light emitting device of the present invention each including 2 or more light emitting layers.
Fig. 2 shows an organic light emitting device in which a substrate 0, a cathode 1, an electron transport layer 2, a hole blocking layer or electron adjusting layer 7, a light emitting layer 1(11), an organic layer 5, a light emitting layer 2(12), a hole transport layer 3, and an anode 4 are sequentially stacked in a vertical direction. In one embodiment of the present specification, the compound represented by the above chemical formula 1 is contained in the organic layer 5 or the hole transport layer 3. In one embodiment, the compound represented by the above chemical formula 2 is contained in the electron transport layer 2, the hole blocking layer or the electron adjusting layer 7, or the organic layer 5.
Fig. 3 shows an organic light emitting device in which a substrate 0, a cathode 1, an electron transport layer 2, a hole blocking layer or electron adjusting layer 7, a light emitting layer 1(11), an organic layer 5, a light emitting layer 2(12), an organic layer 6, a light emitting layer 3(13), a hole transport layer 3, and an anode 4 are sequentially stacked in a vertical direction. In one embodiment of the present specification, the compound represented by the above chemical formula 1 is contained in the organic layer 5, the organic layer 6, or the hole transport layer 3.
Fig. 4 shows an organic light emitting device in which a substrate 0, a cathode 1, an electron transport layer 2, a hole blocking layer or electron adjusting layer 7, a light emitting layer 101, a hole transport layer 3, and an anode 4 are laminated in this order, and the light emitting layer 1(11) and the light emitting layer 2(12) of the light emitting layer 101 are laminated in parallel in the horizontal direction. In one embodiment of the present specification, the compound represented by the above chemical formula 1 is contained in the hole transport layer 3. In one embodiment, the compound represented by the above chemical formula 2 is contained in the electron transport layer 2 or the hole blocking layer or the electron adjusting layer 7.
In one embodiment, the compound represented by the above chemical formula 2 is contained in the electron transport layer 2, the hole blocking layer or the electron adjusting layer 7, the organic layer 5, or the organic layer 6. In one embodiment of the present invention, the light emitting layers 1(11), 2(12) and 3(13) have the same light emitting color. In one embodiment, the light emitting layers 1(11), 2(12) and 3(13) are blue.
When a plurality of light-emitting layers are stacked as shown in fig. 2 and 3, the organic layer provided between the plurality of light-emitting layers may be an intermediate layer. The intermediate layer is also generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron absorption layer, a tie layer, and an intermediate insulating layer, and any layer having a function of supplying electrons to the adjacent layer on the anode side and holes to the adjacent layer on the cathode side can be used. In one embodiment of the present invention, the organic layer 5 located between the light emitting layer 1 and the light emitting layer 2 is a charge generating layer or an intermediate insulating layer. In one embodiment of the present invention, the organic layer 6 located between the light emitting layer 2 and the light emitting layer 3 is a charge generating layer or an intermediate insulating layer.
However, the structure of the organic light emitting device according to one embodiment of the present specification is not limited to fig. 1 to 4, and may be any of the following structures.
(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/luminescent 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/hole regulating layer/light emitting layer/electron transport layer/cathode
(8) Anode/hole transport layer/hole-adjusting layer/light-emitting layer/electron transport layer/electron-injecting layer/cathode
(9) Anode/hole injection layer/hole transport layer/hole regulation layer/light emitting layer/electron transport layer/cathode
(10) Anode/hole injection layer/hole transport layer/hole regulating layer/light emitting layer/electron transport layer/electron injection layer/cathode
(11) Anode/hole transport layer/luminescent layer/electron modulating layer/electron transport layer/cathode
(12) Anode/hole transport layer/luminescent layer/electron modulating layer/electron transport layer/electron injection layer/cathode
(13) Anode/hole injection layer/hole transport layer/light emitting layer/electron modulating layer/electron transport layer/cathode
(14) Anode/hole injection layer/hole transport layer/light-emitting layer 1/intermediate layer/light-emitting layer 2/electron transport layer/electron injection layer/cathode
(15) Anode/hole injection layer/hole transport layer/light-emitting layer 1/intermediate layer/light-emitting layer 2/intermediate layer/light-emitting layer 3/electron transport layer/electron injection layer/cathode
In one embodiment of the present invention, the first organic layer is a light emitting layer, a light emitting layer 1, a light emitting layer 2, or a light emitting layer 3.
When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
The organic layer of the above organic light emitting device may be formed by various methods.
In one embodiment, an organic light emitting device can be manufactured by forming an anode by depositing metal, a metal oxide having conductivity, or an alloy thereof on a substrate, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can function as a cathode on the organic layer.
In another embodiment, an organic light-emitting device may be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (international patent application publication No. 2003/012890). However, the production method is not limited thereto.
The respective organic layers can be formed by any conventional deposition (deposition) technique, such as vapor deposition (vapor deposition), liquid deposition (continuous and discontinuous techniques), and thermal transfer (thermal transfer). The continuous deposition technique includes, but is not limited to, spin coating (spin coating), gravure coating (gravure coating), curtain coating (curve coating), dip coating (dip coating), slit-die coating (slot-die coating), spray coating (spray coating), and continuous nozzle coating (continuous nozzle coating). The discontinuous deposition technique includes an ink jet printing method (ink jet printing), a gravure printing method (gravure printing), and a screen printing method (screen printing), but is not limited thereto.
In one embodiment of the present disclosure, the first organic layer and the second organic layer may be formed by a physical Vapor Deposition method (PVD) such as Vapor Deposition, sputtering, or electron beam evaporation.
According to another embodiment, the first organic layer and the second organic layer may be formed as organic layers by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In one embodiment of the present specification, as other layers in the organic light-emitting device, if the other layers are useful for the respective layers, they can be manufactured using any known substance. Preferred materials suitable for use in the organic layer are exemplified below, but the present invention is not limited thereto.
The anode material is usually used in order to smoothly transfer holes to an organic materialThe layer implant is preferably a substance having a large work function. For example, there are metals such as vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. For example, there are metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic condensed ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a dibenzofuran derivative and a ladder furan compound
Pyrimidine derivatives, etc., but are not limited thereto.
As the dopant material, there are aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, perylene, and the like having an arylamine group,
Diindenopyrene, and the like. Further, the styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine groupAnd substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl and arylamine groups. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The hole injection layer is a layer that receives holes from the electrode. The hole injection substance is preferably as follows: a substance having an ability to transport holes, an effect of receiving holes from the anode, and an excellent hole injection effect for the light-emitting layer or the light-emitting material. Further, a substance having an excellent ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material is preferable. Further, a substance having excellent film-forming ability is preferable. In addition, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include metalloporphyrin (porphyrin), oligothiophene, and arylamine-based organic substances; hexanenitrile hexaazatriphenylene series organic matter; quinacridone (quinacridone) -based organic compounds; perylene (perylene) -based organic compounds; and polythiophene-based conductive polymers such as anthraquinone and polyaniline, but the present invention is not limited thereto.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The electron transport layer receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transport material is a material that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a material having a high electron mobility. Specific examples thereof include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, and hydroxyflavone-metal complexes. The electron transport layer may be used with any desired cathode material as used in the art. In particular, suitable cathode substances are the usual substances having a low work function and accompanied by an aluminum or silver layer. Specifically, there are cesium, barium, calcium, ytterbium, samarium, and the like, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that receives electrons from the electrode. The electron-injecting substance is preferably as follows: a substance which has an excellent ability to transport electrons, has an effect of receiving electrons from the second electrode, and has an excellent electron injection effect for the light-emitting layer or the light-emitting material. Further, it is preferable that the exciton generated in the light-emitting layer is prevented from migrating to the hole-injecting layer and that the thin film-forming ability is excellent. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The electron blocking layer is a layer that prevents electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer to improve the lifetime and efficiency of the device. Any known material can be used without limitation, and the light-emitting layer and the hole-injecting layer or the light-emitting layer and the layer which performs hole injection and hole transport simultaneously can be formed therebetween.
The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed under the same conditions as those of the electron injection layer. Specifically, there are
An oxadiazole derivative or a triazole derivative, a phenanthroline derivative, an aluminum complex (aluminum complex), and the like, but the present invention is not limited thereto.
The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
Modes for carrying out the invention
Hereinafter, the present specification will be described in detail with reference to examples. However, the embodiments described in the present specification may be modified into various forms, and the scope of the present application should not be construed as being limited to the embodiments described in detail below. The embodiments of the present application are provided to more fully explain the present specification to those skilled in the art.
Production example 1-1: production of Compound D1
A flask containing 1-bromo-2, 3-dichlorobenzene (22.6g), intermediate D1-A (21.4g), Pd (PtBu3)2(1.02g), NaOtBu (38.4g) and toluene (800ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate D1-B (12.4g) was obtained. As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 323.
A1.7M solution of tert-butyllithium pentane (9.2ml) was added to a flask containing intermediate D1-B (4.8g) and tert-butylbenzene (160ml) at 0 ℃ under argon. After the end of the dropwise addition, the temperature was raised to 70 ℃ and stirred for 4 hours, whereby the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, warmed to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to the solution to obtain D1(2.3 g). As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 297.
Production examples 1 and 2: production of Compound D2
A flask containing 3-bromo-4, 5-dichlorophenol (24.2g), intermediate D2-A (33.8g), Pd (PtBu3)2(1.02g), NaOtBu (38.4g) and toluene (800ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate D2-B (39.4g) was obtained. As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 463.
A1.7M solution of tert-butyllithium pentane (9.2ml) was added to a flask containing intermediate D2-B (6.9g) and tert-butylbenzene (160ml) at 0 ℃ under argon. After the end of the dropwise addition, the temperature was raised to 70 ℃ and stirred for 4 hours, whereby the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, warmed to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to give intermediate D2-C (3.2 g). As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] -437.
Intermediate D2-C (2.8g), nonafluorobutane-1-sulfonyl fluoride (2.2g) and potassium carbonate (1.5g) were dissolved in acetonitrile (40ml), heated to 50 ℃ and stirred for 4 hours. After cooling to room temperature, distilled water was poured in to remove potassium carbonate, thereby obtaining intermediate D2-D (4.3 g).
A flask containing intermediate D2-D (10.7g), intermediate B-5(2.5g), Pd (PtBu3)2(0.10g), NaOtBu (3.0g) and toluene (100ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain D2(6.2 g). As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ]. 588.
Production examples 1 to 3: production of Compound D3
A flask containing 3-bromo-4, 5-dichlorophenol (24.2g), intermediate D3-A (56.2g), Pd (PtBu3)2(1.02g), NaOtBu (38.4g) and toluene (800ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate D3-B (47.2g) was obtained. As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] -687.
A1.7M solution of tert-butyllithium pentane (9.2ml) was added to a flask containing intermediate D3-B (10.2g) and tert-butylbenzene (160ml) at 0 ℃ under argon. After the end of the dropwise addition, the temperature was raised to 70 ℃ and stirred for 4 hours, whereby the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, warmed to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to give intermediate D3-C (4.9 g). As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] -661.
Intermediate D3-C (4.2g), nonafluorobutane-1-sulfonyl fluoride (2.2g) and potassium carbonate (1.5g) were dissolved in acetonitrile (40ml), heated to 50 ℃ and stirred for 4 hours. After cooling to room temperature, distilled water was poured in to remove potassium carbonate, thereby obtaining intermediate D3-D (5.8 g).
A flask containing intermediate D3-D (14.0g), intermediate C-5(2.5g), Pd (PtBu3)2(0.10g), NaOtBu (3.0g) and toluene (100ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain D3(7.7 g). As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 810.
Production examples 1 to 4: production of Compound D4
A flask containing 1-bromo-2, 3-dichloro-5-methylbenzene (24.0g), intermediate D4-A (28.8g), Pd (PtBu3)2(0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate D4-B (33.0g) was obtained. As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 440.
A flask containing intermediate D4-B (19.3g), intermediate D4-C (18.1g), Pd (PtBu3)2(0.22g), NaOtBu (8.42g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain intermediate D4-D (18.0 g). As a result of mass spectrometry of the obtained solid, a peak was confirmed at [ M + H + ] ═ 817.
A1.7M solution of tert-butyllithium pentane (9.2ml) was added to a flask containing intermediate D4-D (12.2g) and tert-butylbenzene (160ml) at 0 ℃ under argon. After the end of the dropwise addition, the temperature was raised to 70 ℃ and stirred for 4 hours, whereby the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, warmed to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain D4(6.4 g). As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] -791.
Production examples 1 to 5: production of Compound D5
A flask containing 1-bromo-2, 3-dichloro-5-methylbenzene (24.0g), intermediate D5-A (56.4g), Pd (PtBu3)2(1.02g), NaOtBu (38.4g) and toluene (800ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate D5-B (99.8g) was obtained. As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 685.
A1.7M solution of tert-butyllithium pentane (9.2ml) was added to a flask containing intermediate D5-B (10.2g) and tert-butylbenzene (160ml) at 0 ℃ under argon. After the end of the dropwise addition, the temperature was raised to 70 ℃ and stirred for 4 hours, whereby the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, warmed to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to the solution to obtain D5(5.2 g). As a result of mass spectrometry of the obtained solid, a peak was observed at 659 [ M + H + ].
Production examples 1 to 6: production of Compound D6
A flask containing 1-bromo-2, 3-dichloro-5-methylbenzene (24.0g), intermediate D6-A (17.3g), Pd (PtBu3)2(0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate D6-B (24.6g) was obtained. As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 328.
A flask containing intermediate D6-B (14.4g), intermediate D6-C (14.7g), Pd (PtBu3)2(0.22g), NaOtBu (8.42g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain intermediate D6-D (14.0 g). As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] -627.
A1.7M solution of tert-butyllithium pentane (9.2ml) was added to a flask containing intermediate D6-D (9.4g) and tert-butylbenzene (160ml) at 0 ℃ under argon. After the end of the dropwise addition, the temperature was raised to 70 ℃ and stirred for 4 hours, whereby the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, warmed to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain D6(4.4 g). As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 601.
Production examples 1 to 7: production of Compound D7
A flask containing 1-bromo-2, 3-dichloro-5-methylbenzene (22.6g), intermediate D7-A (28.8g), Pd (PtBu3)2(0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate D7-B (30.1g) was obtained. As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] -426.
A flask containing intermediate D7-B (18.7g), intermediate D7-C (15.4g), Pd (PtBu3)2(0.22g), NaOtBu (8.42g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain intermediate D7-D (15.5 g). As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 741.
A1.7M solution of tert-butyllithium pentane (9.2ml) was added to a flask containing intermediate D7-D (11.1g) and tert-butylbenzene (160ml) at 0 ℃ under argon. After the end of the dropwise addition, the temperature was raised to 70 ℃ and stirred for 4 hours, whereby the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, warmed to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to the solution to obtain D7(5.2 g). As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 715.
Production examples 1 to 8: production of Compound D8
A flask containing 1-bromo-2, 3-dichlorobenzene (22.6g), intermediate D8-A (16.9g), Pd (PtBu3)2(0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate D8-B (25.5g) was obtained. As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 315.
A flask containing intermediate D8-B (20.0g), intermediate D8-C (13.9g), Pd (PtBu3)2(0.33g), NaOtBu (12.23g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. The reaction solution was cooled to room temperature, and after adding a saturated solution of NH4Cl (sat. aq.) and toluene and separating the solution, the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain intermediate D8-D (9.8 g). As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 497.
A1.7M solution of tert-butyllithium pentane (9.2ml) was added to a flask containing intermediate D8-D (7.4g) and tert-butylbenzene (160ml) at 0 ℃ under argon. After the end of the dropwise addition, the temperature was raised to 70 ℃ and stirred for 4 hours, whereby the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, warmed to room temperature and stirred for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to the solution to obtain D8(2.2 g). As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] -471.
Production example 2-1: preparation of Compound E1
E1-A (20g, 43.6mmol) and E1-B (10.5g, 43.6mmol) were added to 400ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (18.1g, 130.9mmol) was dissolved in 18ml of water and added, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (1.5g, 1.3mmol) was added. After the reaction for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was added to and dissolved in 20 times 468mL of chloroform, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, and the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give compound E1(13.1g, 56%, MS: [ M + H ] + ═ 537) as a white solid.
Production example 2-2: preparation of Compound E2
The compound E2 was produced by the same method as in production example 2-1, except that the starting materials were used as in the reaction formula.
MS:[M+H]+＝614
Production examples 2 to 3: preparation of Compound E3
The compound E3 was produced by the same method as in production example 2-1, except that the starting materials were used as in the reaction formula.
MS:[M+H]+＝639
Production examples 2 to 4: preparation of Compound E4
The compound E4 was produced by the same method as in production example 2-1, except that the starting materials were used as in the reaction formula.
MS:[M+H]+＝716
Production examples 2 to 5: preparation of Compound E5
The compound E5 was produced by the same method as in production example 2-1, except that the starting materials were used as in the reaction formula.
MS:[M+H]+＝640
Production examples 2 to 6: preparation of Compound E6
The compound E6 was produced by the same method as in production example 2-1, except that the starting materials were used as in the reaction formula.
MS:[M+H]+＝746
Production examples 2 to 7: preparation of Compound E7
The compound E7 was produced by the same method as in production example 2-1, except that the starting materials were used as in the reaction formula.
MS:[M+H]+＝729
Production examples 2 to 8: preparation of Compound E8
The compound E8 was produced by the same method as in production example 2-1, except that the starting materials were used as in the reaction formula.
MS:[M+H]+＝795
Production examples 2 to 9: preparation of Compound E9
The compound E9 was produced by the same method as in production example 2-1, except that the starting materials were used as in the reaction formula.
MS:[M+H]+＝763
Production examples 2 to 10: preparation of Compound E10
The compound E10 was produced by the same method as in production example 2-1, except that the starting materials were used as in the reaction formula.
MS:[M+H]+＝808
Production examples 2 to 11: preparation of Compound E11
The compound E11 was produced by the same method as in production example 2-1, except that the starting materials were used as in the reaction formula.
MS:[M+H]+＝741
Production examples 2 to 12: preparation of Compound E12
The compound E12 was produced by the same method as in production example 2-1, except that the starting materials were used as in the reaction formula.
MS:[M+H]+＝679
Production examples 2 to 13: preparation of Compound E13
E13-A (20g, 34.2mmol) and E13-B (18.4g, 68.4mmol) were added to 400ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (14.2g, 102.7mmol) was dissolved in 14ml of water and added, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (1.2g, 1mmol) was added. After the reaction for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was added to 20 times 544mL of chloroform and dissolved, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto and stirred, and then filtered and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give compound E13(18g, 66%, MS: [ M + H ] + ═ 795) as a white solid.
Experimental example 1-1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone and methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, the following compound HI-A was added
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, HAT compound is sequentially added
Is formed by vacuum evaporation to form a first hole transport layer, and a compound HT-A
The second hole transport layer is formed by vacuum evaporation. On the hole transport layer, the following compound HT-B and
the electron blocking layer is formed by vacuum evaporation. On the above electron blocking layer, the following compound BH and the compound D1 previously prepared were mixed in a weight ratio of 25:1
The thickness of (2) is vacuum-evaporated to form a blue light-emitting layer. On the blue light-emitting layer, the compound E1 prepared above was added
The electron transport layer is formed by vacuum evaporation. On the above electron transport layer, the following compound ET-A and lithium (Li) were added in a weight ratio of 100:1
The electron injection layer is formed by vacuum evaporation. On the electron injection layer, aluminum is added
Is deposited to form a cathode.
In the above process, the evaporation rate of the organic material is maintained at 0.4-0.4
Aluminum maintenance of cathode
The vapor deposition rate of (2), the degree of vacuum of which is maintained at 1X 10 during vapor deposition-7To 5X 10-5And thus an organic light emitting device was manufactured.
Examples 1-2 to 1-104
An organic light-emitting device was produced in the same manner as in example 1-1, except that in example 1-1, compounds of table 1 below were used instead of compound D1 and/or E1.
Comparative examples 1-1 to 1-21
An organic light-emitting device was produced in the same manner as in example 1-1, except that in example 1-1, compounds of table 1 below were used instead of compound D1 and/or E1.
For the organic light emitting devices manufactured in the above examples and comparative examples, at 10mA/cm2The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm2The time required for 90% to the initial brightness was measured at the current density of (1) (T90). The results are shown in table 1 below.
[ Table 1]
As can be seen from table 1 above, the organic light emitting device including all the compounds of chemical formulas 1 and 2 has characteristics of high efficiency, low voltage, and long life. Specifically, it can be seen that when examples 1-1 to 1-104 of the present invention are compared with comparative examples 1-1 to 1-8, devices have low voltage and long life characteristics by including the compound of chemical formula 2 of the present invention, and when examples 1-1 to 1-104 of the present invention are compared with comparative examples 1-9 and 1-21, devices have high efficiency characteristics by including the compound of chemical formula 1 of the present invention. Therefore, if the compound of chemical formula 1 having high efficiency characteristics is used together with the compound of chemical formula 2 having low voltage and long life characteristics, the characteristics that the compound of chemical formula 1 and the compound of chemical formula 2 lack are mutually compensated, so that a more excellent device can be realized.
Claims (17)
1. An organic light emitting device comprising:
an anode;
a cathode; and
a first organic layer and a second organic layer between the anode and the cathode,
wherein the first organic layer includes a compound represented by the following chemical formula 1; and is
The second organic layer includes a compound represented by the following chemical formula 2:
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
x is B; p ═ O; or P is equal to S,
z1 to Z3, which may be the same or different from each other, are each independently a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring,
a1 is N (R101) or O, A2 is N (R102) or O, and
r101 and R102 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combine with each other with an adjacent substituent to form a substituted or unsubstituted ring,
chemical formula 2
In the chemical formula 2,
y is O or S, and Y is O or S,
r21 to R24, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are represented by the following chemical formula 3, or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring,
at least one of R21 to R24 is represented by the following chemical formula 3,
r21 to R24 are the same or different and each independently an integer of 0 to 4, R21 is 2 or more, R21 are the same or different from each other, R22 is 2 or more, R22 is the same or different from each other, R23 is 2 or more, R23 is the same or different from each other, R24 is 2 or more, R24 is the same or different from each other,
chemical formula 3
In the chemical formula 3, the first and second organic solvents,
x1 is N or C (R31), X2 is N or C (R32), X3 is N or C (R33), at least one of X1 to X3 is N,
r31, R32 and R33 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or forms a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring in combination with Ar1 or Ar2,
ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group substituted or unsubstituted with R41, or a heterocyclic group substituted or unsubstituted with R42, or combined with R31, R32, or R33 to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,
r41 and R42, which may be the same or different from each other, are each independently one member selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a halogenated alkyl group, an alkoxy group, a silyl group, an aryl group and a heterocyclic group, or a group formed by connecting 2 or more of the above-mentioned substituents,
l is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,
m is an integer of 0 to 4, and when m is 2 or more, L's are the same or different from each other,
and a site binding to chemical formula 2.
2. The organic light emitting device according to claim 1, wherein the chemical formula 3 is represented by any one of the following chemical formulas 301 to 303:
chemical formula 301
Chemical formula 302
Chemical formula 303
In the chemical formulae 301 to 303,
l, m, Ar1 and Ar2 are as defined in chemical formula 3,
more than one of X1 to X3 is N, and the rest is CH or CD,
r30 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
r30 is an integer of 0 to 4, and when R30 is 2 or more, R30 may be the same as or different from each other.
3. The organic light emitting device according to claim 1, wherein the chemical formula 2 is represented by any one of the following chemical formulae 201 to 204:
chemical formula 201
Chemical formula 202
Chemical formula 203
Chemical formula 204
In the chemical formulae 201 to 204,
x1 to X3, L, m, Ar1, Ar2, R21 to R24, R21 to R24 and Y are as defined in chemical formula 2,
x4 is N or C (R34), X5 is N or C (R35), X6 is N or C (R36), at least one of X4 to X6 is N,
r34, R35 and R36 are the same as or different from each other, and each independently is hydrogen or deuterium, or combines with Ar3 or Ar4 to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring,
ar3 and Ar4 are the same as or different from each other, and each independently represents an aryl group substituted or unsubstituted with R43, or a heterocyclic group substituted or unsubstituted with R44, or combined with R34, R35, or R36 to form a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,
r43 and R44, which may be the same or different from each other, are each independently one member selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a halogenated alkyl group, an alkoxy group, a silyl group, an aryl group and a heterocyclic group, or a group formed by connecting 2 or more of the above-mentioned substituents,
l11 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,
m11 is an integer of 0 to 4, and when m11 is 2 or more, L11 are the same as or different from each other.
4. The organic light emitting device according to claim 1, wherein the chemical formula 2 is represented by any one of the following chemical formulae 211 to 218:
chemical formula 211
Chemical formula 212
Chemical formula 213
Chemical formula 214
Chemical formula 215
Chemical formula 216
Chemical formula 217
Chemical formula 218
In the chemical formulae 211 to 218,
x1 to X3, L, m, Ar1, Ar2, R21 to R24, R21 to R24 and Y are as defined in chemical formula 2.
5. The organic light emitting device according to claim 1, wherein the chemical formula 2 is represented by any one of the following chemical formulae 401 to 403:
chemical formula 401
Chemical formula 402
Chemical formula 403
In the chemical formulae 401 to 403,
x1 to X3, L, m, Ar1, Ar2, R21, R22, R24, R21, R22, R24 and Y are as defined in chemical formula 2,
r25 and R26, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
r25 and R26 are the same as or different from each other and each independently an integer of 0 to 6, and when R25 is 2 or more, R25 are the same as or different from each other, and when R26 is 2 or more, R26 are the same as or different from each other.
6. The organic light emitting device according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 101 to 108:
chemical formula 101
Chemical formula 102
Chemical formula 103
Chemical formula 104
Chemical formula 105
Chemical formula 106
Chemical formula 107
Chemical formula 108
In the chemical formulae 101 to 108,
x, A1 and A2 are as defined in chemical formula 1,
q is O, S, Se, N (R51) or C (R52) (R53),
r11 to R20 and R51 to R53, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring,
r11 and R12 are integers of 0 to 4, and when R11 and R12 are 2 or more, R11 and R12 may be the same as or different from each other,
r13 is an integer of 0 to 3, and when R13 is 2 or more, R13 are the same or different from each other,
r14 to R20 are integers of 0 to 6, and when R14 to R20 are 2 or more, R14 to R20 may be the same as or different from each other.
7. The organic light emitting device of claim 1, wherein X is B, A1 is N (R101), A2 is N (R102),
r101 and R102 are the same or different from each other and are each independently C1-C10 alkyl or C6-C30 aryl substituted or unsubstituted with C1-C10 alkyl.
8. The organic light emitting device according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
9. the organic light emitting device according to claim 1, wherein the compound represented by chemical formula 2 is any one selected from the group consisting of:
10. the organic light emitting device according to claim 1, wherein the compound represented by chemical formula 2 is any one selected from the group consisting of:
11. the organic light emitting device according to claim 1, wherein the compound represented by chemical formula 2 is any one selected from the group consisting of:
12. the organic light emitting device of claim 1, wherein the first organic layer is a light emitting layer.
13. The organic light emitting device according to claim 1, wherein the first organic layer is a light emitting layer including a dopant substance including the compound represented by chemical formula 1.
14. The organic light emitting device of claim 12, further comprising 1 or more light emitting layers.
15. The organic light emitting device according to claim 12, further comprising 1 or more light emitting layers that show a maximum light emission peak in a wavelength range different from a wavelength range of the maximum light emission peak shown in the light emitting layer including the compound represented by chemical formula 1.
16. The organic light emitting device according to claim 12, wherein the light emitting layer comprising the compound represented by chemical formula 1 further comprises a fluorescent dopant.
17. The organic light-emitting device according to claim 15, wherein the 1 or more light-emitting layers that exhibit a maximum light emission peak in a wavelength range different from a wavelength range of the maximum light emission peak exhibited by the light-emitting layer comprising the compound represented by chemical formula 1 comprise a phosphorescent dopant.
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| CN105431439A (en) * | 2014-02-18 | 2016-03-23 | 学校法人关西学院 | Polycyclic aromatic compound |
| KR101755986B1 (en) * | 2016-02-23 | 2017-07-07 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| CN107406758A (en) * | 2015-03-16 | 2017-11-28 | 株式会社Lg化学 | Organic luminescent device |
| CN107851724A (en) * | 2015-03-24 | 2018-03-27 | 学校法人关西学院 | Organic electric-field light-emitting element |
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| TWI661029B (en) * | 2017-03-30 | 2019-06-01 | 南韓商Ｌｇ化學股份有限公司 | Organic light emitting device |
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| CN105431439A (en) * | 2014-02-18 | 2016-03-23 | 学校法人关西学院 | Polycyclic aromatic compound |
| CN107406758A (en) * | 2015-03-16 | 2017-11-28 | 株式会社Lg化学 | Organic luminescent device |
| CN107851724A (en) * | 2015-03-24 | 2018-03-27 | 学校法人关西学院 | Organic electric-field light-emitting element |
| KR101755986B1 (en) * | 2016-02-23 | 2017-07-07 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| CN108290854A (en) * | 2016-02-23 | 2018-07-17 | 株式会社Lg化学 | Heterocyclic compound and organic luminescent device comprising it |
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