CN112969695A - Compound and organic light emitting device including the same - Google Patents
Compound and organic light emitting device including the same Download PDFInfo
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- CN112969695A CN112969695A CN201980070978.6A CN201980070978A CN112969695A CN 112969695 A CN112969695 A CN 112969695A CN 201980070978 A CN201980070978 A CN 201980070978A CN 112969695 A CN112969695 A CN 112969695A
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- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical class C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical class O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 238000009740 moulding (composite fabrication) Methods 0.000 description 1
- KLZHUQDVWUXWEZ-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1.C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 KLZHUQDVWUXWEZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000002919 oxepanes Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- NQFOGDIWKQWFMN-UHFFFAOYSA-N phenalene Chemical compound C1=CC([CH]C=C2)=C3C2=CC=CC3=C1 NQFOGDIWKQWFMN-UHFFFAOYSA-N 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000003077 quantum chemistry computational method Methods 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
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- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- AFYJRAFRYWVOOZ-UHFFFAOYSA-N spiro[cyclopentane-1,9'-fluorene] Chemical compound C1CCCC21C1=CC=CC=C1C1=CC=CC=C12 AFYJRAFRYWVOOZ-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000004882 thiopyrans Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- H10K50/00—Organic light-emitting devices
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Abstract
The present specification provides a compound represented by chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present invention claims priority of korean patent application No. 10-2018-0152177 filed on 30.11.2018 from korean patent office, the entire contents of which are incorporated herein.
The present specification relates to a compound and an organic light emitting device formed using the same.
Background
The organic light emitting device has a structure in which an organic thin film is disposed between 2 electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the 2 electrodes are combined in the organic thin film to be paired, and then quenched and emitted. The organic thin film may be formed of a single layer or a plurality of layers as necessary.
As a substance used in an organic light-emitting device, a pure organic substance or a complex compound of an organic substance and a metal is mainly used, and can be classified into a hole injecting substance, a hole transporting substance, a light-emitting substance, an electron transporting substance, an electron injecting substance, and the like according to the use. Here, as the hole injecting substance or the hole transporting substance, an organic substance having a p-type property, that is, an organic substance which is easily oxidized and has an electrochemically stable state at the time of oxidation is mainly used. On the other hand, as the electron injecting substance or the electron transporting substance, an organic substance having an n-type property, that is, an organic substance which is easily reduced and has an electrochemically stable state at the time of reduction is mainly used. The light-emitting layer material is preferably a material having both p-type and n-type properties, that is, a material having a stable form in both an oxidized state and a reduced state, and is preferably a material having high light emission efficiency in which holes and electrons are recombined in the light-emitting layer to generate excitons (exitons) which are converted into light.
In order to improve the performance, lifetime, or efficiency of organic light emitting devices, development of materials for organic thin films is continuously required.
Disclosure of Invention
Technical subject
The present specification provides compounds and organic light emitting devices comprising the same.
Means for solving the problems
One embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-described chemical formula 1,
x and Y, equal to or different from each other, are each independently O or S,
z is N or CR, and the compound is,
r, R1 to R5, and R7 are the same as or different from each other, and are each independently hydrogen, a nitrile group, deuterium, a halogen group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group(s) (R)
Alkyl thioaxy), substituted or unsubstituted arylthio(s) ((R)
Aryl thio), substituted or unsubstituted alkylsulfonyl(s) ((s)
Alkyl sulfoxy), substituted or unsubstituted arylsulfonyl(s) ((s)
Aryl sulfoxy), a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted Aryl group, or a substituted or unsubstituted heteroaryl group, or may be combined with adjacent groups to each other to form a substituted or unsubstituted ring,
m and n are each independently an integer of 0 to 4, R1 are the same or different from each other when m is 2 or more, R4 are the same or different from each other when n is 2 or more,
o, p, q and w are each independently an integer of 0 to 3, when o is 2 or more, R2 are the same or different from each other, when p is 2 or more, R3 are the same or different from each other, when q is 2 or more, R5 are the same or different from each other, and when w is 2 or more, R7 are the same or different from each other.
In addition, an embodiment of the present specification provides an organic light emitting device including: a first electrode, a second electrode, and 1 or more organic layers between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound of formula 1.
Effects of the invention
The compound described in this specification can be used as a material for an organic layer of an organic light-emitting device. The compound according to at least one embodiment may achieve an improvement in efficiency, a low driving voltage, and/or an improvement in lifetime characteristics in an organic light emitting device. The compound described in this specification can be used as a material for a light-emitting layer.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10, and a cathode 4 are sequentially stacked.
Figure 3 is the MS data for compound 1.
Figure 4 is the MS data for compound 4.
Figure 5 is the MS data for compound 10.
[ description of symbols ]
1: substrate
2: anode
3: luminescent layer
4: cathode electrode
5: hole injection layer
6: hole transport layer
7: electron blocking layer
8: hole blocking layer
9: electron transport layer
10: electron injection layer
Detailed Description
The present specification will be described in more detail below.
One embodiment of the present specification provides a compound represented by the above chemical formula 1.
In the present specification, when a heterocyclic ring formed of a five-membered ring containing X of the above chemical formula 1 is included, the rigidity (rigidity) of the compound included in the organic light emitting device may be improved, and thus the heat resistance of the organic light emitting device may be improved. In addition, it is thereby possible to have high quantum efficiency, and the glass transition temperature is increased, thereby having an advantage that the lifetime characteristics of the organic light emitting device can be improved.
In the present specification, the two benzene rings constituting the heterocyclic ring containing X of the above chemical formula 1 are each substituted with an n-type substituent and a p-type substituent.
In the present specification, when the two benzene rings constituting the heterocyclic ring containing X of the above chemical formula 1 are each substituted at an asymmetric position by an n-type substituent and a p-type substituent, amorphous (amophorus) characteristics are more preferably exhibited, whereby damage of the device due to crystallization caused by joule (joule) heat generated at the time of starting the organic light emitting device can be prevented.
The term "asymmetrically substituted" means that the two benzene rings constituting the heterocycle containing X of the above chemical formula 1 are not substituted by the same carbon number as indicated below.
In this specification, n-type refers to n-type semiconductor characteristics. In other words, n-type refers to a property of injecting or transporting electrons through a LUMO (lowest unoccupied molecular orbital) level, which can be defined as a property of a substance in which mobility of electrons is greater than mobility of holes. In contrast, p-type refers to p-type semiconductor characteristics. In other words, p-type refers to a property of injecting or transporting holes through a HOMO (highest occupied molecular orbital) level, and can be defined as a property of a substance in which the mobility of holes is greater than that of electrons.
In the present specification, when the compound represented by the above chemical formula 1 is used for an organic layer of an organic light emitting device, not only efficiency of the organic light emitting device is improved, but also a driving voltage is low, and life characteristics are excellent.
In particular, the present invention can reduce the voltage of the organic light emitting device by including the compound represented by the above chemical formula 1 and the thermally activated delayed fluorescence compound in an organic layer of the organic light emitting device.
In the present specification, HOMO (highest occupied molecular orbital) refers to a molecular orbital function (highest occupied molecular orbital) of a region with the highest energy in which an electron is located in a region that can participate in binding, LUMO (lowest unoccupied molecular orbital) refers to a molecular orbital function (lowest unoccupied molecular orbital) of a region with the lowest energy in which an electron is located in an anti-binding region, and HOMO level refers to a distance from a vacuum level to HOMO. Further, the LUMO level refers to the distance from the vacuum level to the LUMO.
In the present specification, the bandgap (bandgap) refers to the difference in energy levels of HOMO and LUMO, that is, refers to the HOMO-LUMO energy Gap (Gap).
In the present specification, the HOMO level of the compound represented by the above chemical formula 1 is 6.2eV to 5.5eV, and the LUMO level is 2.8eV to 2.3eV, having appropriate values, and thus the voltage of the organic light emitting device can be reduced when used together with the thermally activated delayed fluorescence compound.
In the present specification, particularly, when a dibenzofuranyl group is introduced based on a heterocyclic ring containing X of the above chemical formula 1, HOMO and LUMO energy levels have appropriate values, so that the voltage of the organic light emitting device can be reduced.
In the present specification, the HOMO level can be measured by UV photoelectron spectroscopy (UV photoelectron spectroscopy) which measures the ionization potential of a substance by irradiating UV to the surface of a thin film and detecting electrons (electrons) emitted at that time. Alternatively, the HOMO level can be measured by a CV (cyclic voltammetry) method in which a target substance for measurement is dissolved in a solvent together with an electrolyte solution, and then an oxidation potential (oxidation potential) is measured by a voltage sweep (voltage sweep). In the case of measuring the HOMO level of the thin film form, the UPS can measure a more accurate value than the CV, and the HOMO level in the present specification is measured by the UPS method.
In the present specification, the LUMO energy level can be determined by measurement of IPES (Inverse Photoelectron Spectroscopy) or electrochemical reduction potential (electrochemical reduction potential). IPES is a method in which an electron beam (electron beam) is irradiated to a thin film, and the LUMO level is determined by measuring the light emitted at this time. In addition, the electrochemical reduction potential may be measured by dissolving the measurement target substance in a solvent together with the electrolyte solution and then measuring the reduction potential (reduction potential) by voltage sweep (voltage sweep). Alternatively, the LUMO level can be calculated from the singlet level obtained by measuring the HOMO level and the degree of UV absorption of the target substance.
In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.
In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the other member but also a case where the other member exists between the two members.
Examples of the above-mentioned substituent are described below, but the substituent is not limited thereto.
In the present specification, the term "substituted or unsubstituted" means substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boryl group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an arylphosphino group, and a heteroaryl group, or with substituents formed by connecting 2 or more substituents among the above-exemplified substituents. 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, an "adjacent" group means a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest to the substituent in terms of a steric structure, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted in 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, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40.
In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms.
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25.
In the present specification, the silyl group may be represented by-SiR11R12R13The above chemical formula (II) represents11、R12And R13And may each be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In 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 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, a, 5-methylhexyl, etc., but is not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there 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, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 20. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited thereto.
The alkyl group, the alkoxy group and other substituents containing an alkyl moiety described in the present specification are all included in a linear or branched form.
In the present specification, the aryloxy group is not particularly limited, but is preferably an aryloxy group having 6 to 60 carbon atoms. Specifically, phenoxy, biphenyloxy, naphthoxy, binaphthoxy, anthracenoxy, phenanthrenoxy, fluorenyloxy, etc. may be mentioned, but the examples are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. 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, as an example of the arylphosphino group, there is a substituted or unsubstituted monoarylphosphino group, a substituted or unsubstituted diarylphosphino group, or a substituted or unsubstituted triarylphosphino group. The aryl group in the above-mentioned arylphosphino group may be a monocyclic aryl group or a polycyclic aryl group. The above-mentioned arylphosphino group containing 2 or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 40 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. According to one embodiment, the aryl group has 6 to 12 carbon atoms. The monocyclic aryl group may be, but is not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, and the like. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a perylene group, a fluoranthenyl group, a triphenylene group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a phenanthryl group, a perylene group, a triphenylene group, a perylene,
And a group such as a phenyl group, a fluorenyl group, an indenyl group, an acenaphthenyl group, a benzofluorenyl group, or a spirofluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.
When the fluorenyl group is substituted, the compound may be
(Spiro [ cyclopentane-1, 9' -fluorene)])、
(9,9' -Spiro-bis [ fluorene)]) Isospirofluorene group;
(9, 9-dimethylfluorenyl group) and
substituted fluorenyl groups such as (9, 9-diphenylfluorenyl) and the like, but are not limited thereto.
In the present specification, the heteroaryl group is a heteroaryl group containing at least 1 of N, O, S as a heteroatom, and the number of carbon atoms is not particularly limited, but the number of carbon atoms is preferably 2 to 260. According to one embodiment, the heteroaryl group has 2 to 40 carbon atoms. According to one embodiment, the heteroaryl group has 2 to 20 carbon atoms. According to one embodiment, the heteroaryl group has 2 to 12 carbon atoms. Examples of heteroaryl groups include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl,
Azolyl radical, iso
Oxazolyl, thiazolyl, isothiazolyl, triazolyl,
Oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiapyranyl, pyrazinyl, pyranyl, thiadiazolyl,
Oxazinyl, thiazinyl, di
Alkenyl, triazinyl, tetrazinyl, quinolyl
Isoquinolinyl, quinolyl
Quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl
Naphthyridinyl, triazainidyl, indolyl, indolinyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, benzothiazolyl
Azolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, phenazinyl, imidazopyridinyl, and thiophene
Oxazinyl and phenanthridinyl
Phenanthroline (phenonthroline), phenothiazine (phenothiazine), imidazophenanthridine, and the like, benzimidazoloquinazolinyl, benzimidazolophenanthridinyl, and the like, but is not limited thereto.
In the present specification, the aryl group in aryloxy group, arylthio group, arylsulfonyl group, arylphosphino group, aralkyl group, aralkylamino group, aralkenyl group, alkylaryl group, arylamino group, arylheteroarylamino group can be applied to the description about the aryl group.
In the present specification, the alkyl group in the alkylthio group, the alkylsulfonyl group, the aralkyl group, the aralkylamino group, the alkylaryl group, and the alkylamino group can be applied to the above description of the alkyl group.
In the present specification, the alkenyl group in the aralkenyl group can be applied to the above description about the alkenyl group.
In the present specification, the term "form a ring by bonding adjacent groups to each other" means that a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a fused ring thereof is formed by bonding adjacent groups to each other.
In the present specification, an aliphatic hydrocarbon ring means a ring which is not an aromatic ring and is composed of only carbon atoms and hydrogen atoms. Specifically, examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1, 4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and cyclooctene, but are not limited thereto.
In the present specification, the aromatic hydrocarbon ring refers to an aromatic ring composed of only carbon atoms and hydrogen atoms. Specifically, examples of the aromatic ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, perylene,
pentacene, fluorene, indene, acenaphthene, benzofluorene, spirofluorene, etc., but is not limited thereto.
In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing 1 or more heteroatoms. Specifically, examples of the aliphatic heterocyclic ring include ethylene oxide (oxirane), tetrahydrofuran, and 1, 4-bis
Alkanes (1,4-dioxane), pyrrolidines, piperidines, morpholines (morpholinones), oxepanes, azocyclooctanes
Thiocyclooctane
And the like, but are not limited thereto.
In the present specification, an aromatic heterocyclic ring means an aromatic ring containing 1 or more heteroatoms. Specific examples of the aromatic heterocyclic ring include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, and the like,
Oxazole, iso
Oxazole, thiazole, isothiazole, triazole, and the like,
Oxadiazoles, thiadiazoles, dithiazoles, tetrazoles, pyrans, thiopyrans, diazines,
Oxazine, thiazine, II
Alkene, triazine, tetrazine, isoquinoline, quinoline, quinolol, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazindene, indole, indolizine, benzothiazole, benzophenon
Oxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, thiophene
Oxazines, indolocarbazoles, indenocarbazoles, and the like, but are not limited thereto.
According to an embodiment of the present specification, R and R1 to R5 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to each other to form a substituted or unsubstituted ring.
According to an embodiment of the present specification, R is the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may be combined with adjacent groups to form a substituted or unsubstituted ring.
According to an embodiment of the present specification, R is hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may be bonded to an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocyclic ring.
According to an embodiment of the present specification, R is hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or may be bonded to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 40 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 40 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 40 carbon atoms.
According to an embodiment of the present specification, R is hydrogen, 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, or may be bonded to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.
According to an embodiment of the present specification, R is hydrogen, 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, or may be bonded to an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 20 carbon atoms.
According to an embodiment of the present specification, R is hydrogen, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms, or may be bonded to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 12 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 12 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 12 carbon atoms.
According to an embodiment of the present disclosure, R is hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorene, dibenzothiophene, dibenzofuran, or carbazole which may be bonded to each other with an adjacent group.
According to an embodiment of the present specification, R is hydrogen.
According to an embodiment of the present specification, R1 to R5, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may be combined with adjacent groups to form a substituted or unsubstituted ring.
According to an embodiment of the present disclosure, R1 to R5 are the same or different and each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may be bonded to each other with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocyclic ring.
According to an embodiment of the present disclosure, R1 to R5 are the same or different and each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or may be bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 40 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 40 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 40 carbon atoms.
According to an embodiment of the present disclosure, R1 to R5 are the same or different and each independently hydrogen, 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, or may be bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.
According to an embodiment of the present disclosure, R1 to R5 are the same or different and each independently hydrogen, 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, or may be bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 20 carbon atoms.
According to an embodiment of the present disclosure, R1 to R5 are the same or different and each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms, or may be bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 12 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 12 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 12 carbon atoms.
According to an embodiment of the present specification, the above R1 to R5 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group, or combine with adjacent groups to form a substituted or unsubstituted ring. According to an embodiment of the present disclosure, R1 to R5, which may be the same or different, are each independently hydrogen, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group, or may be combined with an adjacent group to form a substituted or unsubstituted fluorene, dibenzothiophene, dibenzofuran, or carbazole.
According to an embodiment of the present disclosure, R1 is hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present specification, R1 represents hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.
According to an embodiment of the present specification, R1 represents hydrogen, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
According to an embodiment of the present specification, R1 represents hydrogen, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms.
According to an embodiment of the present disclosure, R1 is hydrogen.
According to an embodiment of the present disclosure, R1 is an aryl group having 6 to 12 carbon atoms substituted with one or more groups selected from deuterium, a nitrile group, an alkyl group, an aryl group, and a heteroaryl group.
According to an embodiment of the present disclosure, R1 is a heteroaryl group having 2 to 12 carbon atoms substituted with one or more groups selected from deuterium, a nitrile group, an alkyl group, an aryl group, and a heteroaryl group.
According to one embodiment of the present specification, R1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted anthracenyl group.
According to one embodiment of the present specification, R1 is a phenyl group substituted or unsubstituted with an alkyl group, a biphenyl group substituted or unsubstituted with an alkyl group, a naphthyl group substituted or unsubstituted with an alkyl group, a terphenyl group substituted or unsubstituted with an alkyl group, or an anthracenyl group substituted or unsubstituted with an alkyl group.
According to an embodiment of the present specification, R1 is a phenyl group substituted or unsubstituted with an aryl group, a biphenyl group substituted or unsubstituted with an aryl group, a naphthyl group substituted or unsubstituted with an aryl group, a terphenyl group substituted or unsubstituted with an aryl group, or an anthracenyl group substituted or unsubstituted with an aryl group.
According to one embodiment of the present specification, R1 is a phenyl group substituted or unsubstituted with a heteroaryl group, a biphenyl group substituted or unsubstituted with a heteroaryl group, a naphthyl group substituted or unsubstituted with a heteroaryl group, a terphenyl group substituted or unsubstituted with a heteroaryl group, or an anthracenyl group substituted or unsubstituted with a heteroaryl group.
According to an embodiment of the present specification, R1 represents hydrogen, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.
According to an embodiment of the present specification, R1 is hydrogen, a phenyl group, or a carbazolyl group.
According to an embodiment of the present specification, R2 is hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may be bonded to each other with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocyclic ring.
According to an embodiment of the present specification, R2 represents hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 40 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 40 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 40 carbon atoms, which may be bonded to each other with an adjacent group.
According to an embodiment of the present specification, R2 represents hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms, which may be bonded to each other with an adjacent group.
According to an embodiment of the present specification, R2 represents hydrogen, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 20 carbon atoms, which may be bonded to each other with an adjacent group.
According to an embodiment of the present specification, R2 represents hydrogen, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 12 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 12 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 12 carbon atoms, which may be bonded to each other with an adjacent group.
According to an embodiment of the present specification, R2 represents hydrogen, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms.
According to one embodiment of the present specification, R2 and an adjacent group are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 20 carbon atoms.
According to another embodiment, R2 is hydrogen, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group, or may be bonded to each other with an adjacent group to form a substituted or unsubstituted fluorene, dibenzothiophene, dibenzofuran, or carbazole.
According to another embodiment, R2 is hydrogen, phenyl or carbazolyl, or may be bonded to an adjacent group to form methyl-substituted fluorene, dibenzothiophene, dibenzofuran, or phenyl-substituted carbazole.
According to an embodiment of the present disclosure, R3 to R5 are the same or different and each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present disclosure, R3 to R5 are the same or different and each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.
According to an embodiment of the present disclosure, R3 to R5 are the same or different and each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
According to an embodiment of the present disclosure, R3 to R5 are the same or different and each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms.
According to an embodiment of the present disclosure, R3 to R5 are the same or different and each independently hydrogen, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.
According to another embodiment, the above R3 to R5, which are the same or different from each other, are each independently hydrogen, phenyl or carbazolyl.
According to another embodiment, the above R3 to R5 are hydrogen.
According to an embodiment of the present disclosure, R7 is hydrogen.
According to an embodiment of the present disclosure, R3 is a substituted or unsubstituted aryl group.
According to an embodiment of the present disclosure, R4 is a substituted or unsubstituted aryl group.
According to an embodiment of the present disclosure, R5 is a substituted or unsubstituted aryl group.
According to an embodiment of the present disclosure, R3 is substituted or unsubstituted heteroaryl.
According to an embodiment of the present disclosure, R4 is substituted or unsubstituted heteroaryl.
According to an embodiment of the present disclosure, R5 is substituted or unsubstituted heteroaryl.
According to an embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 2 or 3.
[ chemical formula 2]
[ chemical formula 3]
In the above chemical formula 2 and chemical formula 3,
x, Y, Z, R, R1 to R5, R7, m, n, o, p, q and w are as defined in the above chemical formula 1.
According to an embodiment of the present disclosure, the chemical formula 1 is represented by the following chemical formula 4.
[ chemical formula 4]
In the above-mentioned chemical formula 4,
y, R1 to R5, R7, m, n, p, q and w are as defined in the above chemical formula 1,
X1is O or S, and is a compound of,
X2o, S, CR ' R ' or NR ',
r ', R', and R6 are defined as R, R1 to R5 and R7 in the above chemical formula 1,
r is an integer of 0 to 2, and when R is 2, R2 are the same or different from each other,
s is an integer of 0 to 4, and when s is 2 or more, R6 may be the same or different from each other.
According to an embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 2-1 or 3-1.
[ chemical formula 2-1]
[ chemical formula 3-1]
In the above chemical formulas 2-1 and 3-1,
y, R1 to R5, m, n, p and q are as defined in the above chemical formula 1,
X1is O or S, and is a compound of,
X2o, S, CR ' R ' or NR ',
r ', R', and R6 are defined as R, R1 to R5 and R7 in the above chemical formula 1,
r is an integer of 0 to 2, and when R is 2, R2 are the same or different from each other,
s is an integer of 0 to 4, and when s is 2 or more, R6 may be the same or different from each other.
According to an embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 2-1-1 to 2-1-6.
[ chemical formula 2-1-1]
[ chemical formula 2-1-2]
[ chemical formulas 2-1-3]
[ chemical formulas 2-1-4]
[ chemical formulas 2-1-5]
[ chemical formulas 2-1-6]
In the above chemical formulas 2-1-1 to 2-1-6,
y, R1 to R5, m, n, p and q are as defined in the above chemical formula 1,
X1is O or S, and is a compound of,
X2o, S, CR ' R ' or NR ',
r ', R', and R6 are defined as R, R1 to R5 and R7 in the above chemical formula 1,
r is an integer of 0 to 2, and when R is 2, R2 are the same or different from each other,
s is an integer of 0 to 4, and when s is 2 or more, R6 may be the same or different from each other.
According to an embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 3-1-1 to 3-1-6.
[ chemical formula 3-1-1]
[ chemical formula 3-1-2]
[ chemical formulas 3-1-3]
[ chemical formulas 3-1-4]
[ chemical formulas 3-1-5]
[ chemical formulas 3-1-6]
In the above chemical formulas 3-1-1 to 3-1-6,
y, R1 to R5, m, n, p and q are as defined in the above chemical formula 1,
X1is O or S, and is a compound of,
X2o, S, CR ' R ' or NR ',
r ', R', and R6 are defined as R, R1 to R5 and R7 in the above chemical formula 1,
r is an integer of 0 to 2, and when R is 2, R2 are the same or different from each other,
s is an integer of 0 to 4, and when s is 2 or more, R6 may be the same or different from each other.
According to an embodiment of the present disclosure, the R ', R ", and R'" are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
According to another embodiment, the above R ', R ", and R'" are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.
According to an embodiment of the present invention, R ', R ", and R'" are the same or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, the above R ', R ", and R'" are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
According to another embodiment, the above R ', R ", and R'" are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
According to an embodiment of the present disclosure, the R ', R ", and R'" are the same or different from each other, and each is independently an alkyl group or an aryl group.
According to another embodiment, the above R ', R ", and R'" are the same or different from each other, and each is independently an alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 40 carbon atoms.
According to an embodiment of the present invention, R ', R ", and R'" are the same or different and each independently an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
According to an embodiment of the present invention, R ', R ", and R'" are the same or different and each independently an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
According to an embodiment of the present invention, R ', R ", and R'" are the same or different and each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms.
According to an embodiment of the present invention, R ', R ", and R'" are the same or different and each independently a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a fluorenyl group, or a pyrenyl group.
According to an embodiment of the present invention, R ', R ", and R'" are the same or different from each other, and each is independently a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, or a tert-butyl group.
According to an embodiment of the present invention, R ', R ", and R'" are the same or different from each other, and are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a fluorenyl group, or a pyrenyl group.
According to an embodiment of the present invention, R ', R ", and R'" are the same or different and each independently methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, or anthracenyl.
According to another embodiment, the above R ', R "and R'" are the same or different from each other and are each independently methyl or phenyl.
In one embodiment of the present specification, R' and R "are methyl.
In one embodiment of the present specification, the above R' and R "are phenyl groups.
In one embodiment of the present specification, R' "is methyl.
In one embodiment of the present disclosure, R' "is a phenyl group.
According to an embodiment of the present disclosure, R6 is hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present specification, R6 represents hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.
According to an embodiment of the present specification, R6 represents hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present specification, R6 represents hydrogen, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
According to an embodiment of the present specification, R6 represents hydrogen, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 12 carbon atoms.
According to an embodiment of the present specification, R6 represents hydrogen, an aryl group having 6 to 40 carbon atoms, or a heteroaryl group having 2 to 40 carbon atoms.
According to an embodiment of the present specification, R6 represents hydrogen, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present specification, R6 represents hydrogen, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms.
According to an embodiment of the present specification, R6 represents hydrogen, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 2 to 12 carbon atoms.
According to an embodiment of the present specification, R6 represents hydrogen, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.
According to an embodiment of the present specification, R6 represents hydrogen, a phenyl group substituted or unsubstituted with an alkyl group or an aryl group, or a carbazolyl group substituted or unsubstituted with an alkyl group or an aryl group.
According to another embodiment, R6 is hydrogen, phenyl or carbazolyl.
According to an embodiment of the present disclosure, R6 is hydrogen.
According to an embodiment of the present disclosure, R7 is hydrogen.
In one embodiment of the present specification, X is O.
In one embodiment of the present specification, X is 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, Z is N.
In one embodiment of the present specification, Z is CR.
In another embodiment, X is as defined above1Is O.
In another embodiment, X is as defined above1Is S.
In one embodiment of the present specification, X is2Is O.
In one embodiment of the present specification, X is2Is S.
In one embodiment of the present specification, X is2Is CR' R ".
In one embodiment of the present specification, X is2Is NR' ".
In one embodiment of the present specification, the chemical formula 1 may be any one selected from the following compounds.
Modes for carrying out the invention
The compound according to one embodiment of the present specification can be produced by a production method described later. This is for the purpose of facilitating understanding, and the method for producing the compound of the present invention is not limited to the following production method.
For example, the compound of chemical formula 1 may have a nucleation structure as shown in the following reaction formula. The substituents may be combined according to a method known in the art, and the kind, position or number of the substituents may be changed according to a technique known in the art.
In the above-mentioned reaction formula, the reaction,
means that additional substituents may be incorporated.
Synthesis of intermediate A
0.4mol of 4-bromodibenzofuran or 4-bromodibenzothiophene, 0.2mol of iodine (iododine) and 0.2mol of diethyliodobenzene (phenyliodoxide diacetate) were added to a mixed solution of 150ml of acetic acid and 150ml of acetic anhydride under a nitrogen atmosphere, three drops of sulfuric acid were added, and then, the mixture was stirred at room temperature for ten hours. After completion of the reaction, ethyl acetate was added to the mixed solution, followed by washing with water, separating the layers, and anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added to the organic layer alone and stirred. After filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure and subjected to column purification, whereby intermediate a was obtained in a yield of 65%.
Synthesis of intermediate B
0.2mol of intermediate A, 0.2mol of carbazole, 0.3mol of copper powder (copper powder) and 0.2mol of potassium carbonate were added to 70ml of dimethylacetamide and stirred at 130 ℃ for 24 hours. After the reaction, the reaction mixture was cooled to room temperature, and then filtered through a silica pad (silica pad) to remove copper powder (copper powder), and the obtained solution was washed with water, and then anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added to only the organic layer, followed by stirring. After filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure and subjected to column purification, whereby intermediate B was obtained in 78% yield.
Synthesis of Compounds C1 and C2
0.3mol of intermediate B, 0.33mol of 1 (or 4) -dibenzofuran (or dibenzothiophene) boronic acid and 2 mol% of tetrakis (triphenylphosphine) palladium (tetra kis (triphenylphoshine) palladium) were added to 50ml of tetrahydrofuran, and 0.6mol of potassium carbonate was dissolved in 25ml of water and mixed. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was taken, and anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred. After filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure and subjected to column purification, whereby compounds C1 and C2 were obtained in a yield of 60%.
In addition, the present specification provides an organic electroluminescent device comprising the above-mentioned compound.
In an embodiment of the present application, there is provided an organic electroluminescent device, including: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound.
The organic layer of the organic electroluminescent device of the present application may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, as a representative example of the organic electroluminescent device of the present invention, the organic electroluminescent 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, and the like as an organic layer. However, the structure of the organic electroluminescent device is not limited thereto, and a smaller number of organic layers may be included.
In one embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.
In one embodiment of the present application, the light-emitting layer includes a host and a dopant.
In one embodiment of the present application, the light-emitting layer contains the compound as a host.
In one embodiment of the present application, the light-emitting layer contains the compound as a phosphorescent host.
In one embodiment of the present application, the light emitting layer includes a host and a dopant at a mass ratio of 99:1 to 1: 99.
In one embodiment of the present application, the light emitting layer includes a host and a dopant at a mass ratio of 99:1 to 10: 90. .
In one embodiment of the present application, the light emitting layer includes a host and a dopant at a mass ratio of 99:1 to 45: 55.
In one embodiment of the present application, the light-emitting layer may use a metal complex as a dopant, but is not limited thereto.
In one embodiment of the present application, the light-emitting layer uses an iridium complex as a dopant.
In one embodiment of the present application, the light-emitting layer may use the iridium complex described below as a dopant, but the light-emitting layer is merely an example and is not limited thereto.
In another embodiment, the light emitting layer including the compound represented by the above chemical formula 1 includes the compound represented by the above chemical formula 1 as a host, and may include a thermally activated delayed fluorescence compound as a dopant.
In the present specification, the thermally activated delayed fluorescence compound means a compound showing generation of a triplet from the lowest excited state (T) by thermal activation1) Excitation of singlet state (S) to the lowest1) The phenomenon of fluorescence emission is realized by reverse energy transfer of (2).
In the present specification, the delayed fluorescence refers to fluorescence in which triplet excitons emit light by Reverse-Intersystem crossing (Reverse-Intersystem crossing) to singlet excitons.
In the present specification, the lowest excited triplet state (T)1) Is the energy of the triplet state with the lowest energy.
In the present specification, the triplet state (triplet state) refers to a state in which the sum of the quantum numbers of the rotational angular momentum of the entire electron is 1.
In this specification, the lowest excited singlet state (S)1) The energy of the singlet state with the lowest energy.
In this specification, a singlet state (singlets state) refers to a state in which the sum of the quantum numbers of rotational angular momentum possessed by the entire electron is 0.
In the present specification, the lowest excited triplet state (T)1) And the lowest excited singlet state (S)1) Is determined by quantum chemical calculations.
The photoluminescence spectrum in the solid state (energy level of the lowest excited singlet state) and the photoluminescence spectrum in the low temperature state (energy level of the lowest excited triplet state) were measured by using LS-55 of Perkin Elmer, the photoluminescence spectrum in the solid state was measured, the photoluminescence spectrum of the excitation (excitation) wavelength at 370nm was 400 to 660nm, HPLC-grade THF was used as the solvent, and the content of the above-mentioned compound was 1 × 10-6And M. The photoluminescence spectrum in the low temperature state was measured by LS-55 of Perkin Elmer (Perkin Elmer), and the excitation wavelength was 400nm to 700nm at 445 nm. The solvent used was HPLC grade THF (tetrahydrofuran) in liquid nitrogenMeasured as follows.
In the present specification, the lowest excited triplet state (T) of a thermally activated delayed fluorescence compound1) And the lowest excited singlet state (S)1) Difference of difference (Delta E)st) Preferably 0.2eV or less (0 eV is not included).
In the present specification, the lowest excited triplet state (T)1) And the lowest excited singlet state (S)1) Difference of difference (Delta E)st) When the amount is small, preferably 0.2eV or less, the singlet excitons emit light as they are (i.e., fluoresce), and the triplet excitons emit light (i.e., delay fluorescence) by Reverse-Intersystem crossing (Reverse-Intersystem crossing) to the singlet excitons. Therefore, a delayed fluorescence mechanism is added to the luminescence based on the fluorescence mechanism, and thus it is possible to achieve an increase in the internal quantum efficiency to 100%.
Lowest excited triplet (T)1) And the lowest excited singlet state (S)1) Difference of difference (Delta E)st) When the amount is larger than 0.2eV, reverse intersystem crossing is relatively less likely to occur, and thus delayed fluorescence may occur less frequently.
In the present specification, the energy (Eg) of the singlet state of the delayed type actinic compound is thermally activatedS) And energy at 77K (Eg)77K) The difference can be represented by the following formula.
△ST＝EgS-Eg77K<0.3eV
In the above formula, EgSAnd Eg77KWhen the difference between the values measured by the above-mentioned singlet and triplet level measurement methods is small and the above formula is satisfied, the reverse intersystem crossing is more smoothly realized, and delayed fluorescence is generated.
In the present specification, the mixture of the compound represented by the above chemical formula 1 and the thermally activated retardation type photochemical compound is composed of-HOMO (host) -I for the purpose of preventing formation of an emission layer exciplex (exiplex)>L-HOMO (TADF) -expression, S1(Host)>2.8eV, preferably HOMO (host) ≧ 5.8 eV.
The exciplex (exiplex) of the light-emitting layer is a complex in which excited and ground molecules of two different molecules are bonded to each other.
In one embodiment of the present specification, when the compound represented by chemical formula 1 and the thermally activated delayed fluorescence compound are used together, the compound of chemical formula 1 may be 99 to 45 parts by weight based on 100 parts by weight of the main body, and the thermally activated delayed fluorescence compound may be 1 to 55 parts by weight based on 100 parts by weight of the main body.
In one embodiment of the present specification, the thermally activated delayed fluorescence compound may be any one selected from the following compounds, but is not limited thereto.
In one embodiment of the present application, the organic layer includes a hole injection layer or a hole transport layer.
In one embodiment of the present invention, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer contains the compound.
In one embodiment of the present application, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.
In one embodiment of the present application, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound.
In one embodiment of the present application, the organic layer includes an electron transport layer or an electron injection layer.
In one embodiment of the present invention, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.
In one embodiment of the present application, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.
In one embodiment of the present application, the organic layer includes an electron blocking layer or a hole blocking layer.
In one embodiment of the present invention, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the compound.
In one embodiment of the present application, the organic electroluminescent device includes a first electrode; a second electrode provided to face the first electrode; a light-emitting layer provided between the first electrode and the second electrode; the organic light emitting device includes 2 or more organic layers between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, and at least one of the 2 or more organic layers contains the compound.
In another embodiment, the organic electroluminescent device may be an organic electroluminescent device having a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.
In another embodiment, the organic electroluminescent device may be an inverted (inverted) type organic electroluminescent device in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.
For example, fig. 1 shows an example of the structure of an organic electroluminescent device according to an embodiment of the present application.
Fig. 1 illustrates the structure of an organic electroluminescent device in which a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 are sequentially stacked. In the structure as described above, the above-described compound may be contained in the above-described light-emitting layer 3.
Fig. 2 illustrates a structure of an organic electroluminescent device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10, and a cathode 4 are sequentially stacked.
The organic electroluminescent device of the present application may be manufactured by materials and methods known in the art, except that 1 or more of the organic layers contain the compound of the present application, i.e., the above-mentioned compound.
When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
The organic light emitting device according to the present invention may be manufactured as follows: the organic el display device is manufactured by forming an anode by depositing metal or a metal oxide having conductivity or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as sputtering or electron beam evaporation, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
In addition, the light-emitting layer can be formed not only by a vacuum deposition method but also by a solution coating method in the production of an organic light-emitting device. The solution coating method is not limited to spin coating, dip coating, blade coating, screen printing, inkjet printing, spraying, and roll coating.
In one embodiment of the present application, 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.
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. As the anode which can be used in the present inventionSpecific examples of the substance include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDT), 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. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injecting substance is a substance that can inject holes from the anode well at a low voltage, and preferably, the HOMO (highest occupied molecular orbital) of the hole 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, but are not limited to, metalloporphyrin (porphyrine), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, and conductive polymers of polyaniline and polythiophene.
The hole-transporting substance is a substance that can receive holes from the anode or the hole-injecting layer and transfer them 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-transporting substance is a substance capable of injecting electrons from the cathode and transferring the electrons to the light-emitting layer, and is preferably a substance having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto.
The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
The method for producing the compound of chemical formula 1 and the production of an organic light emitting device using the same are specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
< production example >
Production example of Compound 1
Synthesis of intermediate 1-1
10g (40.65mmol) of 4-bromodibenzofuran, 5.1g (20.32mmol) of iodine (iododine) and 6.6g (20.32mmol) of diethyliodobenzene were added to a mixed solution of 150ml of acetic acid and 150ml of acetic anhydride under a nitrogen atmosphere, three drops of sulfuric acid were added, and the mixture was stirred at room temperature for ten hours. After completion of the reaction, ethyl acetate was added to the mixed solution, followed by washing with water, separating the layers, and anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added to the organic layer alone and stirred. After filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure and subjected to column purification, whereby intermediate 1-1 was obtained in a yield of 65%.
Synthesis of intermediate 1-2
9.8g (26.35mmol) of intermediate 1, 2.2g (13.18mmol) of carbazole, 2g (32.53mmol) of copper powder (copper powder) and 3.6g (26.35mmol) of potassium carbonate were added to 70ml of dimethylacetamide and stirred at 130 ℃ for 24 hours. After the reaction, the reaction mixture was cooled to room temperature, and then filtered through a silica pad (silica pad) to remove copper powder (copper powder), and the obtained solution was washed with water, and then anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added to only the organic layer, followed by stirring. After filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure and subjected to column purification, whereby intermediate 1-2 was obtained in 78% yield.
Synthesis of Compound 1
8.4g (20.43mmol) of intermediate 1-2, 4.76g (22.47mmol) of dibenzo [ b, d ] furan-4-ylboronic acid and 2 mol% of tetrakis (triphenylphosphine) palladium (tetrapkis (triphenylphoshine) palladium) were added to 50ml of tetrahydrofuran, and 40.86mmol of potassium carbonate was dissolved in 25ml of water and stirred. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to normal temperature, and the water and organic layers were separated. Only the organic layer was taken, and anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred. After filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure and subjected to column purification to obtain compound 1 in a yield of 60%.
MS:[M+H]+＝500
Figure 3 is the MS data for compound 1.
Production example of Compound 2
Synthesis of Compound 2
MS:[M+H]+＝500
Production example of Compound 3
Synthesis of Compound 3
MS:[M+H]+＝516
Production example of Compound 4
Synthesis of intermediate 4-1
5g (12.16mmol) of intermediate 1-2, 3.7g (14.59mmol) of bis (pinacolato) diboron, 2.39g (24.32mmol) of potassium acetate, 4 mol% of bis (dibenzylideneacetone) palladium (bis (dibenzylideneacetone) palladium) and 0.27g (0.97mmol) of tricyclohexylphosphine were added to 50ml of dicyclohexylphosphine
In an alkane, stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto, followed by stirring, filtration through a silica gel pad (silica pad) and concentration under reduced pressure. Column purification was performed to obtain intermediate 4-1 in a yield of 85%.
Synthesis of Compound 4
MS:[M+H]+＝665
Figure 4 is the MS data for compound 4.
Production example of Compound 5
Synthesis of intermediate 5-1
Intermediate 5-1 was obtained in 51% yield by conducting a reaction and purification in the same manner as in the synthesis of intermediate 1-2 described above, except that 4.47g (13.45mmol, Cas No.1247053-55-9) of 5-phenyl-5, 12-indolino [3,2-a ] carbazole was used instead of 5g (13.45mmol) of intermediate 1-1 and carbazole.
Synthesis of Compound 5
MS:[M+H]+＝665
Production example of Compound 6
Synthesis of Compound 6
MS:[M+H]+＝665
Production example of Compound 7
Synthesis of intermediate 7-1
An intermediate 7-1 was obtained in a yield of 57% by conducting a reaction and purification in the same manner as in the synthesis of the above intermediate 1-2, except that 5g (13.45mmol) of the intermediate 1-1 and 5.14g (13.45mmol) of 5- (naphthalen-2-yl) -5, 12-indolino [3,2-a ] carbazole were used.
Synthesis of Compound 7
MS:[M+H]+＝731
Production example of Compound 8
Synthesis of intermediate 8-1
Intermediate 8-1 was obtained in 78% yield by conducting a reaction and purification in the same manner as in the synthesis of compound 1 above, except that 10g (47.16mmol) of dibenzo [ b, d ] furan-2-ylboronic acid and 9.48g (47.16mmol) of 1-bromo-2-nitrobenzene were used.
Synthesis of Compound 8-2
10.6g (36.78mmol) of intermediate 8-1 and 90ml of triethyl phosphite (triethylphoshite) were added and stirred under reflux. After stirring for 10 hours, the mixture was cooled to normal temperature and concentrated under reduced pressure. After washing with water and extraction with ethyl acetate, anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added to the organic layer alone, followed by stirring, filtration through a silica gel pad (silica pad) and concentration under reduced pressure. Column purification was performed to obtain intermediate 8-2 in 66% yield.
Synthesis of Compound 8-3
Intermediate 8-3 was obtained in 55% yield by performing a reaction and purification in the same manner as in the synthesis of intermediate 1-2 described above, except that 6.24g (24.27mmol) of intermediate 8-2 and 9.02g (24.27mmol) of intermediate 1-1 were used.
Synthesis of Compound 8
MS:[M+H]+＝590
Production example of Compound 9
Synthesis of intermediate 9-1
10g (38.17mmol) of 4-bromodibenzothiophene, 4.8g (19.08mmol) of iodine (iododine) and 6.1g (19.08mmol) of diethyliodobenzene were added to a mixed solution of 130ml of acetic acid and 150ml of acetic anhydride under nitrogen, three drops of sulfuric acid were added, and the mixture was stirred at room temperature for ten hours. After completion of the reaction, ethyl acetate was added to the mixed solution, followed by washing with water, separating the layers, and anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added to the organic layer alone and stirred. After filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure and subjected to column purification, whereby intermediate 9-1 was obtained in a yield of 53%.
Synthesis of intermediate 9-2
7.8g (20.11mmol) of intermediate 9-1, 3.4g (20.11mmol) of carbazole, 1.8g (30.16mmol) of copper powder (copper powder) and 2.8g (20.11mmol) of potassium carbonate were added to 60ml of dimethylacetamide and stirred at 130 ℃ for 24 hours. After the reaction, the reaction mixture was cooled to room temperature, and then filtered through a silica pad (silica pad) to remove copper powder (copper powder), and the obtained solution was washed with water, and then anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added to only the organic layer, followed by stirring. After filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure and subjected to column purification, whereby intermediate 9-2 was obtained in a yield of 66%.
Synthesis of Compound 9
5.7g (13.34mmol) of intermediate 9-2, 3.1g (14.67mmol) of dibenzo [ b, d ] furan-4-ylboronic acid and 2 mol% of tetrakis (triphenylphosphine) palladium (tetrapkis (triphenylphoshine) palladium) were added to 50ml of tetrahydrofuran, and 40.02mmol of potassium carbonate was dissolved in 25ml of water and stirred. After stirring at 80 ℃ for 12 hours, the reaction was terminated, cooled to room temperature and the water and organic layers were separated. Only the organic layer was taken, and anhydrous magnesium sulfate (anhydrous magnesium sulfate) was added thereto and stirred. After filtration through a silica gel pad (silica pad), the solution was concentrated under reduced pressure and subjected to column purification, whereby 4.3g of compound 9 was obtained in a yield of 62%.
MS:[M+H]+＝516
Preparation example of Compound 10
Synthesis of intermediate 10-1
An intermediate 10-1 was obtained in 58% yield by conducting a reaction and purification in the same manner as in the synthesis of the intermediate 9-2, except that 10g (25.78mmol) of the intermediate 9-1 and 4.9g (25.78mmol) of 9H-carbazole-3-carbonitrile were used.
Synthesis of Compound 10
MS:[M+H]+＝541
Figure 5 is the MS data for compound 10.
< example >
ITO (indium tin oxide) is added
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, or 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, m-MTDATA (60nm)/TCTA (80 nm)/host + 10% Ir (ppy)3(300nm)/BCP(10nm)/Alq3(30nm)/LiF (1nm)/Al (200nm) constituting a light-emitting device in this order, Compound 1 being used as the above-mentioned hostThereby, an organic EL device was manufactured.
m-MTDATA、TCTA、Ir(ppy)3And the structures of BCP are shown below, respectively.
< Experimental examples 1 and 2>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 2 was used instead of the compound 1.
< Experimental examples 1 to 3>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that the compound 3 was used instead of the compound 1 in the experimental example 1-1.
< Experimental examples 1 to 4>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 4 was used instead of the compound 1.
< Experimental examples 1 to 5>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 5 was used instead of the compound 1.
< Experimental examples 1 to 6>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 6 was used instead of the compound 1.
< Experimental examples 1 to 7>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that the compound 7 was used instead of the compound 1 in the experimental example 1-1.
< Experimental examples 1 to 8>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 8 was used instead of the compound 1.
< Experimental examples 1 to 9>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 9 was used instead of the compound 1.
< Experimental examples 1 to 10>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound 10 was used instead of the compound 1.
< comparative example 1-1>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that GH1 was used instead of compound 1 in experimental example 1-1.
< comparative examples 1 and 2>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that GH2 was used instead of compound 1 in experimental example 1-1.
< comparative examples 1 to 3>
An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that GH3 was used instead of compound 1 in experimental example 1-1.
When a current was applied to the organic light emitting devices fabricated using experimental examples 1-1 to 1-10 and comparative examples 1-1 and 1-3, the results of table 1 were obtained.
[ Table 1]
As a result of experiments, the green organic EL devices of experimental examples 1-1 to 1-10 using the compounds represented by the compounds 1 to 10 according to the present invention as host materials of the light emitting layer showed excellent performance in terms of current efficiency and driving voltage, as compared to the green organic EL devices of comparative examples 1-1 to 1-3 using GH1 to GH3 as existing compounds. In the case of compounds 1 to 10, it is characterized in that the 2-position of dibenzofuran or dibenzothiophene is substituted with a substituent having an additional ring fused to the carbazole or at the carbazole, and dibenzofuran or dibenzothiophene is bonded at the 6-position.
In the case of GH1, carbazole and dibenzofuran are bonded to positions 2 and 8 of dibenzofuran, respectively, and GH2 is a compound in which GH1 is further substituted with 2 amine groups.
GH3 is a compound in which carbazole is bonded to the 2-position and dibenzofuran is bonded to the 4-and 6-positions of dibenzofuran or dibenzothiophene.
As can be seen from the above table, such differences can make experimental examples 1-1 to 1-10 have lower voltage and higher efficiency than comparative examples 1-1 to 1-3.
< Experimental example 2-1>
An organic light emitting diode in which compound 1 was applied as a main body of a light emitting substance layer was produced. First, a glass substrate having an ITO (including a reflective plate) electrode attached thereto, which is 40mm × 40mm × 0.5mm thick, was ultrasonically washed with isopropyl alcohol, acetone, and deionized Water (DI Water) for 5 minutes, and then dried in an Oven (Oven) at 100 ℃. After the substrate was washed, O was performed for 2 minutes in a vacuum state2The plasma treatment is carried to the deposition chamber for depositing another layer on the upper part. At about 10-7Organic layers were evaporated in the following order from a heated boat under vacuum by evaporation. At this time, the deposition rate of the organic material is set to
Hole injection layer (HIL; HAT-CN (hexaazatriphenylene hexacyano-nitrile (Hex)aazatriphenylenehexacarbonitrile))，
) A hole transport layer (HTL; NPB (N, N '-bis (naphthalen-1-yl) -N, N' -bis (phenyl) benzidine (N, N '-bis (naphthalen-1-yl) -N, N' -bis (phenyl) -benzidine)),
) Electron blocking layer (EBL; mCBP (3, 3-bis (9H-carbazol-9-yl) biphenyl) (3,3-Di (9H-carbazol-9-yl) biphenol),
) A light emitting substance layer (EML; compound 1 was used as a host, 4CzIPN was used as a delayed fluorescent substance and was doped at 30% by weight,
) Hole blocking layer (HBL; b3PYMPM (4,6-Bis (3,5-di (pyridin-3-yl) phenyl) -2-methylpyrimidine (4,6-Bis (3,5-di (pyridine-3-yl) phenyl) -2-methylpyrimidine));
) Electron transport layer (ETL: TPBi (1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (2,2' - (1,3, 5-benzinetryl) -tris (1-phenyl-1-H-benzimidazole))),
) An electron injection layer (EIL; the reaction mixture of LiF and a metal oxide,
) Cathode (Al;
)。
after forming a capping layer (CPL) using CPL, the resultant was encapsulated with glass. After such a layer is deposited, the film is moved from the deposition chamber into a drying oven to form a coating film, and then encapsulated with a UV curable epoxy resin and a moisture getter (getter).
< Experimental examples 2-2>
An organic light-emitting device was produced in the same manner as in experimental example 2-1, except that in experimental example 2-1, the compound 2 was used instead of the compound 1.
< Experimental examples 2 to 3>
An organic light-emitting device was produced in the same manner as in experimental example 2-1, except that the compound 3 was used instead of the compound 1 in the experimental example 2-1.
< Experimental examples 2 to 4>
An organic light-emitting device was produced in the same manner as in experimental example 2-1, except that in experimental example 2-1, the compound 4 was used instead of the compound 1.
< Experimental examples 2 to 5>
An organic light-emitting device was produced in the same manner as in experimental example 2-1, except that the compound 5 was used instead of the compound 1 in the experimental example 2-1.
< Experimental examples 2 to 6>
An organic light-emitting device was produced in the same manner as in experimental example 2-1, except that the compound 6 was used instead of the compound 1 in the experimental example 2-1. .
< Experimental examples 2 to 7>
An organic light-emitting device was produced in the same manner as in experimental example 2-1, except that the compound 7 was used instead of the compound 1 in the experimental example 2-1.
< Experimental examples 2 to 8>
An organic light-emitting device was produced in the same manner as in experimental example 2-1, except that in experimental example 2-1, the compound 8 was used instead of the compound 1.
< Experimental examples 2 to 9>
An organic light-emitting device was produced in the same manner as in experimental example 2-1, except that in experimental example 2-1, the compound 9 was used instead of the compound 1.
< Experimental examples 2 to 10>
An organic light-emitting device was produced in the same manner as in experimental example 2-1, except that in experimental example 2-1, the compound 10 was used instead of the compound 1.
< comparative example 2-1>
An organic light-emitting device was produced in the same manner as in experimental example 2-1, except that GH4(mCBP) was used instead of compound 1 in experimental example 2-1.
[ Table 2]
Examples 2-1 to 2-10 of the present invention used compounds in which 3 or more heteroaryl groups containing N, S, O were sequentially bonded. In contrast, GH4 of the compound of comparative example 2-1 has biphenyl as a linking group between carbazole and carbazole. When the organic compound synthesized according to the present invention is used as a host for a delayed fluorescence light emitting layer, the driving voltage is reduced and the External Quantum Efficiency (EQE) is improved, as compared with the case where the compound of comparative example 2-1 is used as a host for a light emitting layer.
As a result, it was confirmed that the organic compound of the present invention is applied to an organic light emitting layer, thereby reducing the driving voltage of a light emitting diode, improving the light emitting efficiency, and improving the color purity. Therefore, the organic light emitting diode using the organic compound of the present invention can be used for a light emitting device such as an organic light emitting diode display device and/or a lighting device, which reduces power consumption and improves light emitting efficiency and device lifetime.
Claims (16)
1. A compound represented by the following chemical formula 1:
chemical formula 1
Wherein, in the chemical formula 1,
x and Y are the same or different from each other and are each independently O or S,
z is N or CR, and the compound is,
r, R1 to R5, and R7 are the same as or different from each other, and are each independently hydrogen, a nitrile group, deuterium, a halogen group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups with each other to form a substituted or unsubstituted ring,
m and n are each independently an integer of 0 to 4, and when m is 2 or more, R1 are the same or different from each other, and when n is 2 or more, R4 are the same or different from each other, and
o, p, q and w are each independently an integer of 0 to 3, and when o is 2 or more, R2 are the same or different from each other, when p is 2 or more, R3 are the same or different from each other, when q is 2 or more, R5 are the same or different from each other, and when w is 2 or more, R7 are the same or different from each other.
2. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2 or chemical formula 3:
chemical formula 2
Chemical formula 3
In the chemical formulas 2 and 3,
x, Y, Z, R1 to R5, R7, m, n, o, p, q and w are as defined in said chemical formula 1.
3. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 4:
chemical formula 4
In the chemical formula 4, the first and second organic solvents,
y, R1 to R5, R7, m, n, p, q and w are as defined in said chemical formula 1,
X1is O or S, and is a compound of,
X2o, S, CR ' R ' or NR ',
r ', R', and R6 are defined as R, R1 to R5 and R7 in the chemical formula 1,
r is an integer of 0 to 2, and when R is 2, R2 are the same or different from each other, and
s is an integer of 0 to 4, and when s is 2 or more, R6 may be the same or different from each other.
4. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2-1 or chemical formula 3-1:
chemical formula 2-1
Chemical formula 3-1
In the chemical formulas 2-1 and 3-1,
y, R1 to R5, m, n, p and q are as defined in said chemical formula 1,
X1is O or S, and is a compound of,
X2o, S, CR ' R ' or NR ',
r ', R', and R6 are defined as R, R1 to R5 and R7 in the chemical formula 1,
r is an integer of 0 to 2, and when R is 2, R2 are the same or different from each other, and
s is an integer of 0 to 4, and when s is 2 or more, R6 are the same as or different from each other.
5. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 2-1-1 to 2-1-6:
chemical formula 2-1
Chemical formula 2-1-2
Chemical formula 2-1-3
Chemical formula 2-1-4
Chemical formula 2-1-5
Chemical formula 2-1-6
In the chemical formulas 2-1-1 to 2-1-6,
y, R1 to R5, m, n, p and q are as defined in said chemical formula 1,
X1is O or S, and is a compound of,
X2o, S, CR ' R ' or NR ',
r ', R', and R6 are defined as R, R1 to R5 and R7 in the chemical formula 1,
r is an integer of 0 to 2, and when R is 2, R2 are the same or different from each other, and
s is an integer of 0 to 4, and when s is 2 or more, R6 are the same as or different from each other.
6. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 3-1-1 to 3-1-6:
chemical formula 3-1
Chemical formula 3-1-2
Chemical formula 3-1-3
Chemical formula 3-1-4
Chemical formula 3-1-5
Chemical formula 3-1-6
In the chemical formulas 3-1-1 to 3-1-6,
y, R1 to R5, m, n, p and q are as defined in said chemical formula 1,
X1is O or S, and is a compound of,
X2o, S, CR ' R ' or NR ',
r ', R', and R6 are defined as R, R1 to R5 and R7 in the chemical formula 1,
r is an integer of 0 to 2, and when R is 2, R2 are the same or different from each other, and
s is an integer of 0 to 4, and when s is 2 or more, R6 are the same as or different from each other.
7. The compound of claim 1, wherein R and R1 to R5 are the same or different from each other and are each independently hydrogen, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or combine with each other with adjacent groups to form a substituted or unsubstituted ring.
8. The compound of claim 1, wherein R is hydrogen.
9. The compound of claim 1, wherein the R1 to R5 are the same as or different from each other and are each independently hydrogen, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group, or combine with adjacent groups to each other to form a substituted or unsubstituted ring.
10. The compound of claim 1, wherein the chemical formula 1 is represented by any one of the following structural formulae:
11. an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound according to any one of claims 1 to 10.
12. An organic light-emitting device according to claim 11 wherein the organic layer comprises a light-emitting layer and the light-emitting layer comprises a compound according to any one of claims 1 to 10.
13. An organic light-emitting device according to claim 12 wherein the light-emitting layer comprises the compound of any one of claims 1 to 10 as a phosphorescent host.
14. The organic light-emitting device according to claim 12, wherein the light-emitting layer contains the compound according to any one of claims 1 to 10 as a host, and contains a thermally-activated delayed fluorescence compound as a dopant.
15. An organic light-emitting device according to claim 14 wherein the dopant comprises the lowest excited triplet state T1With the lowest excited singlet S1Energy gap Δ E therebetweenstA thermally activated delayed fluorescence compound having a thermal activation value of 0.2eV or less.
16. The organic light emitting device of claim 14, wherein the thermally activated delayed fluorescence compound is represented by any one of the following structural formulas:
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