WO2023043040A1 - 신규한 발광 소자용 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents
신규한 발광 소자용 화합물 및 이를 포함하는 유기 발광 소자 Download PDFInfo
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- WO2023043040A1 WO2023043040A1 PCT/KR2022/010817 KR2022010817W WO2023043040A1 WO 2023043040 A1 WO2023043040 A1 WO 2023043040A1 KR 2022010817 W KR2022010817 W KR 2022010817W WO 2023043040 A1 WO2023043040 A1 WO 2023043040A1
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- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/04—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D277/62—Benzothiazoles
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- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
Definitions
- the present invention relates to a compound for a light emitting device and an organic light emitting device including the same.
- Materials used as the organic layer in the organic light emitting device can be largely classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like according to their functions.
- the light emitting material is a fluorescent material derived from a singlet excited state of electrons, a phosphorescent material derived from a triplet excited state of electrons, and a delay derived from the movement of electrons from a triplet excited state to a singlet excited state according to a light emitting mechanism. It can be classified as a fluorescent material, and can be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color.
- a typical organic light emitting device may have a structure in which an anode is formed on a substrate, and a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially formed on the anode.
- the hole transport layer, the light emitting layer, and the electron transport layer are organic thin films made of organic compounds.
- the driving principle of the organic light emitting device having the above structure is as follows.
- Efficiency of an organic light emitting device can be generally divided into internal light emitting efficiency and external light emitting efficiency.
- the internal luminous efficiency is related to how efficiently excitons are generated and light conversion is performed in the organic layer interposed between the first electrode and the second electrode, such as the hole transport layer, the light emitting layer, and the electron transport layer.
- the external luminous efficiency indicates the efficiency in which light generated in the organic layer is extracted to the outside of the organic light emitting device, and it is known that about 20% of the internal luminous efficiency is extracted to the outside.
- various organic compounds having a refractive index of 1.7 or higher have been applied as a capping layer to prevent total reflection and loss of light going out to the outside.
- An organic light emitting device including a composite layer structure of a capping layer having a low refractive index and a capping layer having a low refractive index is being developed.
- LiF has been commercialized as a material for a low refractive index capping layer
- the problem of high deposition temperature and poor processability of such inorganic compounds has been pointed out, and efforts are being made to replace them with organic compounds.
- a boron coordination compound is known as a material having a low refractive index, but the boron coordination compound lacks stability, and thus a problem of reducing the lifespan of the organic light emitting device also occurred. Accordingly, efforts are being made to develop an organic capping layer material having excellent compound stability while maintaining a low refractive index.
- An object of the present invention is to provide a compound for a light emitting device including a heterocyclylene core, providing high thermal stability, high efficiency, and long lifespan, and an organic light emitting device including the same.
- the present invention since the present invention has a structure in which two or more amine-based or carbonyl-based substituents are connected through a heterocyclylene group, a low refractive index can be formed, and a particularly wide band gap can be maintained to secure a low attenuation coefficient even in a short wavelength range. It is an object of the present invention to provide a compound for a light emitting device capable of realizing a lower refractive index when applied to a capping layer and an organic light emitting device including the same.
- a substituent having a low polarization rate may be introduced to have a lower refractive index, it is to provide a compound for a light emitting device that is very effective in improving the efficiency and color purity of an organic light emitting device when applied to a capping layer and an organic light emitting device including the same. The purpose.
- thermal stability can be improved by including a heterocyclylene linking group, and at the same time, two or more amine-based or carbonyl-based substituents are linearly connected to have excellent thin film arrangement, so when applied to a capping layer, external oxygen, air, It is an object of the present invention to provide a compound for a light emitting device that is more effective in improving the lifespan of an organic light emitting device and an organic light emitting device including the same with improved stability from contamination such as moisture.
- An object of the present invention is to provide a compound for a light emitting device capable of realizing an organic light emitting device and an organic light emitting device including the same.
- a compound for a light emitting device represented by Formula 1 is provided:
- HetCy is a substituted or unsubstituted C2 ⁇ C50 heterocyclylene group
- L1 and L2 are each independently a direct bond, a substituted or unsubstituted C1-C50 alkylene group, a substituted or unsubstituted C2-C50 alkenylene group, a substituted or unsubstituted C1-C50 alkyleneoxy group, or an ether group.
- R1 to R10 are each independently hydrogen, heavy hydrogen, halogen, nitro group, nitrile group, hydroxyl group, thiol group, substituted or unsubstituted amino group, substituted or unsubstituted C1 ⁇ C50 alkyl group, substituted or unsubstituted C2 ⁇ C50 alkenyl group, substituted or unsubstituted C1 ⁇ C50 alkoxy group, substituted or unsubstituted C1 ⁇ C50 sulfide group, substituted or unsubstituted C0 ⁇ C50 silyl group, substituted or unsubstituted C3 ⁇ C50 A cycloalkyl group, a substituted or unsubstituted C3 ⁇ C50 cycloalkenyl group, a substituted or unsubstituted C1 ⁇ C50 heterocyclyl group, a substituted or unsubstituted C3 ⁇ C50 aryl group, or a substituted or unsubstituted C2
- l is an integer from 0 to 14;
- An organic light-emitting device containing the above-described compound for light-emitting devices is provided.
- the compound for a light emitting device includes a heterocyclylene core and can implement a value light emitting device with high thermal stability, high efficiency, and long lifespan.
- amine-based or carbonyl-based substituents have a structure connected through a heterocyclylene group, a low refractive index can be formed, and a particularly wide band gap can be maintained to secure a low attenuation coefficient even in a short wavelength range.
- a lower refractive index can be realized.
- thermal stability can be improved by including a heterocyclylene linking group, and at the same time, two or more amine-based or carbonyl-based substituents are linearly connected to have excellent thin film arrangement, so when applied to a capping layer, external oxygen, air, It is more effective in improving the lifespan of the organic light emitting device by improving stability from contamination such as moisture.
- a hole injection layer In addition, it is used in one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and an exciton blocking layer, and thus has high color purity, high efficiency, and long lifespan.
- An organic light emitting device of can be implemented.
- FIG. 1 is a schematic cross-sectional view showing a configuration of an organic light emitting device according to an exemplary embodiment of the present invention.
- aryl refers to a C5-50 aromatic hydrocarbon ring group such as phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenyl It means containing an aromatic ring such as renyl, perylenyl, chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzochrysenyl, anthracenyl, stilbenyl, pyrenyl, etc., and "heteroaryl” is a C2-50 aromatic ring containing at least one heteroatom, for example, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzo furanyl, benzothiophenyl, dibenzothi
- Ar x (where x is an integer) means a substituted or unsubstituted C6-C50 aryl group or a substituted or unsubstituted C2-C50 heteroaryl group, unless otherwise defined
- L x (where x is an integer) means a direct bond, a substituted or unsubstituted C6 ⁇ C50 arylene group, or a substituted or unsubstituted C2 ⁇ C50 heteroarylene group, unless otherwise defined
- R x (where x is If not particularly defined, hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C1 ⁇ C30 alkyl group, substituted or unsubstituted C2 ⁇ C30 alkenyl group, substituted or unsubstituted C1 ⁇ C30 alkoxy group, substituted or unsubstituted C1 ⁇ C30 sulfide group, substituted or unsubstituted C
- substituted or unsubstituted refers to deuterium, halogen, amino, cyano, nitrile, nitro, nitroso, sulfamoyl, isothiocyanate, thiocyanate groups.
- An organic light emitting device may include a first electrode, a second electrode, and one or more organic material layers interposed inside the first electrode and the second electrode.
- the compound for a light emitting device of the present invention may be included in any one or more of the organic material layers.
- An organic light emitting device may be an organic light emitting device including a capping layer. Specifically, a first electrode, a second electrode, one or more organic material layers interposed inside the first electrode and the second electrode, and a capping layer disposed outside any one or more of the first electrode and the second electrode. It may be an organic light emitting device that The compound for a light emitting device of the present invention may be included in the capping layer.
- HetCy is a substituted or unsubstituted C2 ⁇ C50 heterocyclylene group
- L1 and L2 are each independently a direct bond, a substituted or unsubstituted C1-C50 alkylene group, a substituted or unsubstituted C2-C50 alkenylene group, a substituted or unsubstituted C1-C50 alkyleneoxy group, or an ether group.
- R1 to R10 are each independently hydrogen, heavy hydrogen, halogen, nitro group, nitrile group, hydroxyl group, thiol group, substituted or unsubstituted amino group, substituted or unsubstituted C1 ⁇ C50 alkyl group, substituted or unsubstituted C2 ⁇ C50 alkenyl group, substituted or unsubstituted C1 ⁇ C50 alkoxy group, substituted or unsubstituted C1 ⁇ C50 sulfide group, substituted or unsubstituted C0 ⁇ C50 silyl group, substituted or unsubstituted C3 ⁇ C50 A cycloalkyl group, a substituted or unsubstituted C3 ⁇ C50 cycloalkenyl group, a substituted or unsubstituted C1 ⁇ C50 heterocyclyl group, a substituted or unsubstituted C3 ⁇ C50 aryl group, or a substituted or unsubstituted C2
- l is an integer from 0 to 14;
- L1 and L2 may each independently be the examples listed above or a combination of three or less of them, specifically, a direct bond, substituted or unsubstituted -CH2-, -O-, -S-, Substituted or unsubstituted -C(X1)-, substituted or unsubstituted -CH2-C(X1)-, substituted or unsubstituted -C(X1)-CH2-, substituted or unsubstituted -C(X1) -O-, substituted or unsubstituted -O-C(X1)-, substituted or unsubstituted -C(X1)-S-, substituted or unsubstituted -S-C(X1)-, substituted or unsubstituted -C( X1)-C(X1)-, substituted or unsubstituted -C(X2)NR3-, substituted or unsubstituted -NR4C(X3)-
- Formula 1 may include a compound for a light emitting device represented by any one of Formulas 2 to 4 below.
- n is an integer from 1 to 5; Specifically, m may be an integer of 1 to 3.
- the compounds for a light emitting device of the present invention represented by Chemical Formulas 2 to 4 may have a low refractive index by including a carbonyl group or an amide bond, and at the same time, have excellent chemical stability and thermal stability.
- m is an integer from 1 to 5. Specifically, m may be an integer of 1 to 3.
- the compound for a light emitting device of the present invention represented by Chemical Formula 5 has a lower refractive index because nitrogen (N) of the amide is included in the heterocyclylene group (HetCy), and at the same time has excellent thermal stability.
- two amide-based linking groups N in the heterocyclylene group may exist asymmetrically skewed in one direction.
- the HetCy may include at least one of nitrogen (N), oxygen (O), and sulfur (S) as a hetero element.
- the hetero elements may include two or more, more specifically, three or more. In this case, it is possible to maintain a low refractive index, which is more effective in improving thermal stability.
- the HetCy (heterocyclylene group) may be selected from the following A-1 to A-10.
- Q and R20 are each independently a methyl group, an ethyl group, a t-butyl group, a cyclohexyl group, an adamantane group, a dihydroamine group, a dimethylamine group, a hydroxyl group, a methoxy group, a mercaptan group, a methylthio group, A fluorine group, a trifluoromethyl group, a nitrile group, a nitro group, or a trimethylsilyl group,
- p is each independently an integer of 1 to 5, specifically may be an integer of 1 to 3,
- n is each independently an integer of 0 to 10, specifically an integer of 0 to 4;
- the HetCy (heterocyclylene group) may be selected from A-11 to A-18 below.
- Q is each independently a methyl group, an ethyl group, a t-butyl group, a cyclohexyl group, an adamantane group, a phenyl group, a dihydroamine group, a dimethylamine group, a hydroxyl group, a methoxy group, a mercaptan group, a methylthio group, A fluorine group, a trifluoromethyl group, a nitrile group, a nitro group, or a trimethylsilyl group,
- p is each independently an integer from 1 to 6;
- n is each independently an integer of 0 to 10, specifically an integer of 0 to 4;
- R1 to R4 may each independently be a substituted or unsubstituted C3-C50 cycloalkyl group or a substituted or unsubstituted C1-C50 heterocyclyl group.
- R1 to R4 may be each independently a substituted C3-C50 cycloalkyl group or a substituted C1-C50 heterocyclyl group. By having a substituted structure, it can have high thermal stability.
- R1 to R4 are not limited, but each independently a hydroxyl group, a thiol group, an amino group, a nitrile group, a nitro group, a C1-C30 alkyl group, a C1-C30 halogenated alkyl group, a C1-C30 alkoxy group, a C1 It may be selected from the group consisting of a ⁇ C30 sulfide group, a C0 ⁇ C30 silyl group, a halogen group, a C3 ⁇ C30 cycloalkyl group, a C3 ⁇ C30 cycloalkenyl group, a C1 ⁇ C30 heterocyclyl group, and combinations thereof. . By having such a substituent, it is possible to maintain a low refractive index and have high thermal stability at the same time.
- R3 and R4 may each independently be hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a C3-C30 cycloalkyl group, or a C1-C30 heterocyclyl group. In this case, it may be effective to improve the deposition temperature by minimizing the molecular weight.
- R3 and R4 may be hydrogen.
- R1 and R2 may not be hydrogen.
- a lower refractive index can be formed by lowering the intramolecular polarizability and at the same time having a low attenuation coefficient even in a short wavelength range.
- l may be 1 or 2. In this case, a low refractive index can be maintained and it can be more effective in improving the deposition temperature.
- At least one of -L1-R1 and -L2-R2 may each independently be selected from the following chemical structural formulas B-1 to B-59.
- W1 is each independently a methyl group, an ethyl group, a t-butyl group, a cyclohexyl group, an adamantane group, a dihydroamine group, a dimethylamine group, a hydroxyl group, a methoxy group, a mercaptan group, a methylthio group, and a fluorine group.
- n is each independently an integer of 0 to 10, specifically an integer of 0 to 4,
- At least one of -L1-R1 and -L2-R2 may each independently be selected from the following chemical structures C-1 to C-14.
- At least one of -L1-R1 and -L2-R2 is a change in the structure of -CO-N-* or -CO-N(CO)-* to -N-* in the above chemical formulas C-1 to C-14. can take the form of a chemical structure.
- the refractive index at a wavelength of 450 nm may have a low refractive index of 1.55 or less.
- the refractive index at a wavelength of 450 nm may have a low refractive index of 1.50 or less, more specifically 1.45 or less.
- Formula 1 may be a compound for a light emitting device represented by any one of the following compounds. Since the following compounds are only examples for explaining the present invention, the present invention is not limited thereto.
- One embodiment of the compound of the present invention can be synthesized by the following schematic reaction scheme.
- the present invention provides an organic light emitting device containing a compound for a light emitting device.
- the organic light emitting device includes a first electrode and a second electrode; It includes one or more organic material layers interposed inside the first electrode and the second electrode, and the compound for the light emitting device may be contained in one or more of the organic material layers.
- the organic material layer containing the compound for the light emitting device may be at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and an exciton blocking layer. there is. Specifically, it may be a hole transport layer, a light emitting auxiliary layer, or a light emitting layer.
- the compound for a light emitting device of the present invention may be used alone or in combination with a known organic light emitting compound.
- the light emitting auxiliary layer is a layer formed between the hole transport layer and the light emitting layer, and may be referred to as a second hole transport layer or a third hole transport layer according to the number of hole transport layers.
- the organic light emitting device includes a first electrode and a second electrode; one or more organic material layers interposed inside the first electrode and the second electrode; A capping layer disposed outside any one or more of the first electrode and the second electrode may be further included, and the compound for the light emitting device may be included in the capping layer.
- the organic light emitting device may include a first electrode, a second electrode, one or more organic material layers interposed inside the first electrode and the second electrode, and a capping layer, wherein the The capping layer may be disposed on an outer side of at least one of the first electrode and the second electrode.
- a side adjacent to the organic material layer interposed between the first electrode and the second electrode is referred to as an inner side
- a side not adjacent to the organic material layer is referred to as an outer side. That is, when the capping layer is disposed outside the first electrode, the first electrode is interposed between the capping layer and the organic layer, and when the capping layer is disposed outside the second electrode, the second electrode is interposed between the capping layer and the organic layer. do.
- one or more layers of various organic materials may be interposed inside the first electrode and the second electrode, and the outer side of any one or more of the first electrode and the second electrode.
- a capping layer may be formed on. That is, the capping layer may be formed on both the outside of the first electrode and the outside of the second electrode, or may be formed only on the outside of the first electrode or the outside of the second electrode.
- the capping layer may include the compound for a light emitting device according to the present invention, and may include the compound for a light emitting device according to the present invention alone, two or more types, or a known compound together.
- the capping layer may have a thickness of 100 ⁇ to 3000 ⁇ .
- the capping layer may have a composite capping layer structure in which a first capping layer having a relatively low refractive index and a second capping layer having a higher refractive index than the first capping layer are stacked.
- the device compound may be included in the first capping layer.
- the stacking order of the first capping layer and the second capping layer is not limited, and the first capping layer may be disposed outside the second capping layer, or conversely, the second capping layer may be disposed outside the first capping layer.
- the second capping layer may be interposed between the first capping layer and the first electrode or the second electrode, and specifically, the second capping layer includes the first capping layer and the first electrode. Alternatively, it may have a structure in contact with the first capping layer and the second electrode.
- first capping layer and the second capping layer may be alternately stacked, and the stacking order is not limited as described above, and the first capping layer may be disposed outside the second capping layer, and vice versa.
- the second capping layer may be disposed outside the first capping layer.
- the first capping layer may have a refractive index of 1.55 or less, specifically 1.50 or less, more specifically 1.45 or less at a wavelength of 450 nm.
- the second capping layer may have a refractive index of 2.10 or more, specifically 2.25 or more, and more specifically 2.30 or more at a wavelength of 450 nm, and the difference between the refractive index of the first capping layer and the second capping layer at a wavelength of 450 nm is 0.2 to 1.2 range, more specifically within the range of 0.4 to 1.2.
- the difference in refractive index is less than 0.2 or greater than 1.2, there is a problem in that light extraction efficiency is lowered.
- the total thickness of the first capping layer may be in the range of 50 ⁇ to 2000 ⁇ , and the total thickness of the second capping layer may be in the range of 50 ⁇ to 2000 ⁇ .
- the capping layer may have a refractive index gradient.
- the refractive index may gradually decrease toward the outside, and the refractive index may gradually increase toward the outside.
- a refractive index gradient may be implemented in the capping layer by forming a capping layer by gradually varying the concentration of the compound for a light emitting device according to the present invention.
- the organic material layer may generally include a hole transport layer, a light emitting layer, and an electron transport layer constituting the light emitting unit, but may not be limited thereto.
- the organic light emitting device includes a hole injection layer (HIL), a hole transport layer (HTL), and a light emitting layer ( EML), an electron transport layer (ETL), and an electron injection layer (EIL) may include one or more organic material layers constituting the light emitting part.
- HIL hole injection layer
- HTL hole transport layer
- EML electron transport layer
- EIL electron injection layer
- ETL electron transport layer
- EIL electron injection layer
- a hole blocking layer (HBL, not shown) or an electron transport auxiliary layer is formed between the light emitting layer (EML) and the electron transport layer (ETL)
- EBL electron blocking layer
- EBL electron blocking layer
- FIG. 1 is a cross-sectional view schematically showing the configuration of an organic light emitting device according to an embodiment of the present invention.
- An organic light emitting device according to an embodiment of the present invention may be manufactured as the structure described in FIG. 1 .
- the organic light emitting device includes a substrate 100, a first electrode 1000, a hole injection layer 200, a hole transport layer 300, a light emitting layer 400, an electron transport layer 500, and an electron injection layer from below. 600, the second electrode 2000, and the capping layer 3000 may be sequentially stacked.
- the capping layer 3000 may have a structure in which a first capping layer and a second capping layer are stacked as described above.
- a third capping layer having a different refractive index from the first capping layer and the second capping layer may be further added to have a stacked structure, but is not limited thereto.
- the capping layer may have a refractive index gradient. In the refractive index gradient, the refractive index may gradually decrease toward the outside, and the refractive index may gradually increase toward the outside.
- the substrate 100 may use a substrate generally used in an organic light emitting device, and in particular, a transparent glass substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance, or a flexible plastic substrate.
- a transparent glass substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance
- a flexible plastic substrate can be
- the first electrode 1000 is used as a hole injection electrode for hole injection of an organic light emitting device.
- the first electrode 1000 is manufactured using a material having a low work function to enable injection of holes, and is formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), or graphene. It can be.
- ITO indium tin oxide
- IZO indium zinc oxide
- graphene graphene
- the hole injection layer 200 is formed by depositing a hole injection layer material on top of the first electrode 1000 by a method such as a vacuum deposition method, a spin coating method, a cast method, a Langmuir-Blodgett (LB) method, and the like It can be.
- the deposition conditions vary depending on the compound used as the material of the hole injection layer 200, the desired structure and thermal characteristics of the hole injection layer 200, etc. In general, a deposition temperature of 50 to 500° C., a vacuum degree of 10 -8 to 10 -3 torr, a deposition rate of 0.01 to 100 ⁇ /sec, and a layer thickness of 10 ⁇ to 5 ⁇ m can be appropriately selected.
- a charge generation layer may be additionally deposited on the surface of the hole injection layer 200 if necessary.
- a conventional material can be used as the material of the charge generation layer, and HATCN is exemplified.
- the hole transport layer 300 may be formed by depositing a hole transport layer material on top of the hole injection layer 200 by a method such as a vacuum deposition method, a spin coating method, a cast method, or an LB method.
- a vacuum deposition method the deposition conditions vary depending on the compound used, but are generally selected within the same range of conditions as those for forming the hole injection layer 200.
- the hole transport layer 300 may be formed using a known compound.
- the hole transport layer 300 may have one or more layers, and although not shown in FIG. 1 , it may include two layers of a first hole transport layer and a second hole transport layer (emission auxiliary layer). At least one of the first hole transport layer and the second hole transport layer may include the compound for a light emitting device according to the present invention.
- the light emitting layer 400 may be formed by depositing a light emitting layer material on top of the hole transport layer 300 or the light emitting auxiliary layer by a method such as a vacuum deposition method, a spin coating method, a cast method, or an LB method.
- a vacuum deposition method the deposition conditions vary depending on the compound used, but are generally selected within the same range of conditions as those for forming the hole injection layer 200.
- the light emitting layer material may use a compound for a light emitting device according to the present invention or a known compound as a host or dopant.
- a compound for a light emitting device may be used as a host and a known compound may be used as a dopant.
- the dopant is not limited, but a phosphorescent or fluorescent dopant may be used together to form the light emitting layer.
- BD142 N6,N12-bis(3,4-dimethylphenyl)-N6,N12-dimethylchrysene-6,12-diamine
- green phosphorescence as a phosphorescent dopant.
- Dopant Ir(ppy)3 tris(2-phenylpyridine)iridium
- UDC's red phosphorescent dopant RD61, etc. can be co-evaporated (doped).
- the doping concentration of the dopant is not particularly limited, but is preferably doped with 0.01 to 15 parts by weight of the dopant based on 100 parts by weight of the host.
- the dopant content is less than 0.01 parts by weight, there is a problem that the dopant amount is not sufficient and the color development is not performed properly, and if it exceeds 15 parts by weight, there is a problem that the efficiency is rapidly reduced due to the concentration quenching phenomenon.
- a hole blocking material is added to the top of the light emitting layer 400 to prevent triplet excitons or holes from diffusing into the electron transport layer 500 by vacuum deposition method or It can be laminated through a spin coating method.
- the hole blocking material that can be used is not particularly limited, and known materials can be arbitrarily selected and used. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or a hole blocking material described in Japanese Patent Laid-Open No.
- the light emitting layer 400 of the present invention may include one or more blue light emitting layers or two or more layers.
- the electron transport layer 500 is formed on the light emitting layer 400, and may be formed by a method such as a vacuum deposition method, a spin coating method, or a cast method.
- the deposition conditions of the electron transport layer 500 vary depending on the compound used, but it is generally preferable to select them within the same range of conditions as those for forming the hole injection layer 200 .
- a light emitting device compound according to the present invention or a conventionally known material may be arbitrarily selected and used.
- quinoline derivatives particularly tris(8-quinolinolato)aluminum (Alq3), or ET4(6,6'-(3,4-dimethyl-1,1- dimethyl-1H-silol-2,5-diyl)di-2,2′-bipyridine) can be used.
- the electron injection layer 600 may be formed by depositing an electron injection layer material on top of the electron transport layer 500, and may be formed by a method such as a vacuum deposition method, a spin coating method, or a cast method.
- a method such as a vacuum deposition method, a spin coating method, or a cast method.
- a compound for a light emitting device according to the present invention or a known material such as LiF, NaCl, CsF, LiO, or BaO may be used.
- the second electrode 2000 is used as an electron injection electrode, and may be formed on top of the electron injection layer 600 by a vacuum deposition method or a sputtering method.
- Various metals may be used as the material of the second electrode 2000 . Specific examples include lithium (Li), aluminum (Al), gold (Au), silver (Ag), magnesium (Mg), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), There is a material such as magnesium-silver (Mg-Ag), but is not limited thereto.
- a transmissive electron injection electrode using ITO or IZO may be used to obtain a top light emitting device.
- the organic light emitting device of the present invention includes the first electrode 1000, the hole injection layer 200, the hole transport layer 300, the light emitting layer 400, the electron transport layer 500, the electron injection layer 600, and the second electrode described above.
- organic light emitting diodes having a structure including (2000) and a capping layer 3000 organic light emitting diodes having various structures are possible, and one or two intermediate layers may be additionally included as needed.
- each organic material layer formed according to the present invention may be adjusted according to a required degree, specifically 1 to 1,000 nm, and more specifically 1 to 150 nm.
- the capping layer 3000 may be formed on an outer surface on which the hole injection layer 200 is not formed among both side surfaces of the first electrode 1000 .
- the electron injection layer 600 may be formed on the outer side of both sides of the second electrode 2000 on which the electron injection layer 600 is not formed, but is not limited thereto.
- the capping layer 3000 may be formed through a deposition process, and may have a thickness of 100 to 3,000 ⁇ , more specifically, 300 to 2,000 ⁇ . Through such thickness control, it is possible to prevent the transmittance of the capping layer 3000 from being lowered.
- an organic material layer may be additionally formed.
- an organic material layer having various functions may be additionally formed on the top (outer surface) of the capping layer 3000, and one or more separate functional layers may be inserted and present in the middle of the capping layer 3000. It is not.
- the present invention is manufactured to have the structure of the organic light emitting device shown in FIG. 1 as an example.
- the manufactured organic light emitting device includes an anode (hole injection electrode 1000) / hole injection layer 200 / hole transport layer 300 / light emitting layer 400 / electron transport layer 500 / electron injection layer 600 from below. ) / cathode (electron injection electrode 2000) / capping layer 3000 are stacked in this order.
- the capping layer 3000 may have a multilayer structure in which the first capping layer and the second capping layer are combined.
- the substrate 10 may be a transparent glass substrate or a flexible plastic substrate.
- the hole injection electrode 1000 is used as an anode for hole injection of an organic light emitting device.
- a material having a low work function is used to enable injection of holes, and it may be formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), or graphene.
- ITO indium tin oxide
- IZO indium zinc oxide
- graphene graphene
- the materials listed in Table 3 were used for the hole injection layer 200, the charge generation layer, the hole transport layer 300, the light emitting layer 400, the electron transport layer 500, the electron injection layer 600, and the high refractive index capping layer.
- a cathode 2000 for electron injection was formed on the electron injection layer 600 .
- Various metals can be used as the cathode. Specific examples include materials such as aluminum, gold, silver, magnesium, and a magnesium-silver alloy.
- ITO indium tin oxide
- a reflective layer containing silver (Ag) was formed was cleaned with ultrasonic waves in distilled water. After washing with distilled water, ultrasonic cleaning was performed using solvents such as isopropyl alcohol, acetone, and methanol, and drying was performed. Thereafter, 100 ⁇ of HT01 and NDP9 were doped with 3% by weight of NDP9 as a hole injection layer on the ITO substrate, and 1000 ⁇ of HT01 as a hole transport layer were deposited, respectively. ⁇ thickness was deposited.
- an electron transport layer a mixture of ET01 and Liq (1:1, wt./wt.) was deposited to a thickness of 300 ⁇ , and then LiF was deposited to a thickness of 10 ⁇ to form an electron injection layer.
- MgAg was deposited to a thickness of 15 nm to form a cathode
- CPM01 was deposited to a thickness of 950 ⁇ as a high refractive capping layer on the cathode
- the compound prepared in Synthesis Example 1 was deposited to a thickness of 400 ⁇ as a low refractive capping layer.
- An organic light emitting device was manufactured by encapsulating the device in a glove box.
- An organic light emitting diode was manufactured in the same manner as in Example 1, but formed with a low refractive index capping layer using the compounds prepared in Synthesis Example 2 to Synthesis Example 25, respectively.
- An organic light emitting diode was manufactured in the same manner as in Example 1, but using Comparative Compounds 1 to 4 shown in Table 4 below, respectively, to form a low refractive index capping layer.
- the present invention can have a low refractive index because it is connected through a heterocyclylene core to form a low polarizability, and has a lower refractive index because two or more amine-based substituents are connected.
- the embodiments of the present invention compared to Example 1 and Example 2, the case where the two amide-based linking groups N in HetCy are asymmetrically biased in one direction is symmetrically opposite to the other. It can have a lower refractive index than the case, it can be seen that it is effective in improving efficiency.
- Example 3 In addition, by comparing Example 3 with Example 4, it can be seen that having an additional substituent has excellent thermal stability and is effective in improving lifespan.
- Example 5 and Example 6 when adamantane is used as a substituent, it is effective in improving life span due to excellent thermal stability, and when a substituent has a cyclohexyl group having a low polarizability, it has a lower refractive index. It can be seen that it is effective in improving efficiency.
- the compounds according to the present invention exhibit a low refractive index of 1.50 or less, specifically 1.45 or less, at a wavelength of 450 nm.
- other compounds according to the present invention also showed a low refractive index of 1.50 or less, more specifically, 1.45 or less at a wavelength of 450 nm.
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Abstract
Description
Op. V | mA/cm2 | Cd/A | CIEx | CIEy | LT97 | |
실시예1 | 3.45 | 10 | 10.15 | 0.140 | 0.043 | 170 |
실시예2 | 3.45 | 10 | 11.15 | 0.140 | 0.042 | 172 |
실시예3 | 3.45 | 10 | 10.27 | 0.139 | 0.043 | 180 |
실시예4 | 3.44 | 10 | 10.23 | 0.139 | 0.043 | 191 |
실시예5 | 3.45 | 10 | 11.41 | 0.139 | 0.042 | 175 |
실시예6 | 3.45 | 10 | 11.20 | 0.139 | 0.042 | 200 |
실시예15 | 3.45 | 10 | 11.46 | 0.139 | 0.042 | 167 |
실시예16 | 3.45 | 10 | 11.44 | 0.139 | 0.042 | 165 |
실시예17 | 3.45 | 10 | 11.32 | 0.140 | 0.042 | 160 |
실시예19 | 3.45 | 10 | 11.10 | 0.139 | 0.042 | 157 |
실시예20 | 3.45 | 10 | 10.10 | 0.140 | 0.043 | 169 |
비교예1 | 3.47 | 10 | 6.77 | 0.134 | 0.053 | 84 |
비교예2 | 3.46 | 10 | 8.01 | 0.135 | 0.048 | 137 |
비교예3 | 3.46 | 10 | 6.84 | 0.137 | 0.053 | 120 |
비교예4 | 3.46 | 10 | 8.10 | 0.137 | 0.048 | 69 |
비교 화합물1 |
비교 화합물2 |
비교 화합물3 |
비교 화합물4 |
화합물 67 |
화합물 68 |
화합물 163 |
화합물 167 |
화합물 214 |
화합물 222 |
|
n@450nm | 1.73 | 1.59 | 1.74 | 1.58 | 1.39 | 1.38 | 1.38 | 1.39 | 1.37 | 1.40 |
Claims (28)
- 하기 화학식 1로 표시되는 발광 소자용 화합물:<화학식1>(HetCy은 치환 또는 비치환된 C2~C50의 헤테로사이클릴렌기이며,L1 및 L2는 각각 독립적으로 직접결합, 치환 또는 비치환된 C1~C50의 알킬렌기, 치환 또는 비치환된 C2~C50의 알케닐렌기, 치환 또는 비치환된 C1~C50의 알킬렌옥시기, 에테르기, 치환 또는 비치환된 C1~C50의 설파이드기, 티오에테르기, 치환 또는 비치환된 C1~C50의 -C(X1)-, 치환 또는 비치환된 -C(X2)NR3-, 치환 또는 비치환된 -NR4C(X3)-, 치환 또는 비치환된 -NR5-, 치환 또는 비치환된 -R6-NR7-, 치환 또는 비치환된 C3~C50의 사이클로알킬렌기, 또는 치환 또는 비치환된 C1~C50의 헤테로사이클릴렌기, 치환 또는 비치환된 C3~C50의 아릴렌기, 또는 치환 또는 비치횐된 C2~C50의 헤테로아릴렌기이거나, 이들의 조합이며,X1 내지 X3는 각각 독립적으로 O, S, Se, Te, =NR8, 또는 =CR9R10이며,R1 내지 R10은 각각 독립적으로 수소, 중수소, 할로겐, 니트로기, 니트릴기, 하이드록시기, 티올기, 치환 또는 비치환된 아미노기, 치환 또는 비치환된 C1~C50의 알킬기, 치환 또는 비치환된 C2~C50의 알케닐기, 치환 또는 비치환된 C1~C50의 알콕시기, 치환 또는 비치환된 C1~C50의 설파이드기, 치환 또는 비치환된 C0~C50의 실릴기, 치환 또는 비치환된 C3~C50의 사이클로알킬기, 치환 또는 비치환된 C3~C50의 사이클로알케닐기, 치환 또는 비치환된 C1~C50의 헤테로사이클릴기, 치환 또는 비치환된 C3~C50의 아릴기, 또는 치환 또는 비치환된 C2~C50의 헤테로아릴기이며, 인접한 복수의 R1 내지 R10은 서로 결합하여 고리를 형성하거나 형성하지 않을 수 있고,l은 0 내지 14의 정수이다).
- 제3항에 있어서,상기 헤테로사이클릴렌기(HetCy) 내의 2개의 아마이드 계열 연결기 N은 비대칭적으로 어느 한 방향으로 치우쳐 존재하는 발광 소자용 화합물.
- 제1항에 있어서,상기 HetCy(헤테로사이클릴렌기)에는 헤테로원소로서 질소(N), 산소(O) 및 황(S) 중에서 하나 이상 포함되는 발광 소자용 화합물.
- 제1항에 있어서,상기 화학식 1의 상기 R1 내지 R4 중 2개 이상은 각각 독립적으로 치환 또는 비치환된 C3~C50의 사이클로알킬기, 또는 치환 또는 비치환된 C1~C50의 헤테로사이클릴기인 발광 소자용 화합물.
- 제1항에 있어서,상기 화학식 1의 상기 R1 내지 R4 중 하나 이상은 각각 독립적으로 치환된 C3~C50의 사이클로알킬기, 또는 치환된 C1~C50의 헤테로사이클릴기인 발광 소자용 화합물.
- 제9항에 있어서,상기 R1 내지 R4의 치환기로는 각각 독립적으로, 하이드록시기, 티올기, 아미노기, 니트릴기, 니트로기, C1~C30의 알킬기, C1~C30의 할로겐화 알킬기, C1~C30의 알콕시기, C1~C30의 설파이드기, C0~C30의 실릴기, 할로겐기, C3~C30의 사이클로알킬기, C3~C30의 사이클로알케닐기, C1~C30의 헤테로사이클릴기 및 이들의 조합으로 이루어진 군에서 선택되는 발광 소자용 화합물.
- 제2항에 있어서,상기 화학식 3 및 화학식 4의 상기 R3 및 R4는 수소인 발광 소자용 화합물.
- 제1항에 있어서,상기 화학식 1에서 상기 l은 1 또는 2인 발광 소자용 화합물.
- 제13항에 있어서,상기 -L1-R1과 -L2-R2 중 하나 이상은 각각 독립적으로 상기 화학 구조식 B-1 내지 B-43에서 -NH-CO-* 구조는 -Z-* 또는 *-Z-로 바뀐 형태의 화학구조식을 취하며, 상기 Z는 -NH-CS-, -NH-CSe-, -NH-CTe-, -NHC(=CH2)-, -NH-CNH-, -NH-CNMe-, -NHC(=CHMe)-, -NHC(=CMe2)-, -CH2NH-CO-, -NH-COCH2-, -CH2NH-COCH2-, -O-NH-CO-, -NH-COO-, -O-NH-COCH2-, -CH2NH-COO-, -O-NH-COO-, -S-NH-CO-, -NH-COS-, -S-NH-COCH2-, -CH2NH-COS-, -S-NH-COS-, -CO-NH-CO-, -NH-CO-CO-, -NH-, -CO-NH-, -CH2-CO-, -CO-CH2-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -CO-CO-, -OCONH-, -CH2-, -O-, -S-, -C0-, -CS-, -C(=NH)-, -C(=NMe)-, -C(=CH2)-, -C(=CHMe)-, -C(=CMe2)-, 또는 - 중에서 선택되는 발광 소자용 화합물.
- 제1항에 있어서,상기 발광 소자용 화합물은 450nm 파장에서의 굴절률이 1.55 이하인 발광 소자용 화합물.
- 제1항의 발광 소자용 화합물을 함유하는 유기 발광 소자.
- 제17항에 있어서,상기 유기 발광 소자는 제1전극 및 제2 전극;상기 제1 전극 및 상기 제2 전극의 내측에 개재되는 1층 이상의 유기물층을 포함하며,상기 발광 소자용 화합물은 상기 유기물층 중 하나 이상에 함유되는 유기 발광 소자.
- 제18항에 있어서,상기 발광 소자용 화합물이 함유되는 유기물층은 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송보조층, 전자수송층 및 전자주입층 중 하나 이상인 유기 발광 소자.
- 제18항에 있어서,상기 발광 소자용 화합물이 함유되는 유기물층은 정공수송층, 발광보조층 또는 발광층인 유기 발광 소자.
- 제17항에 있어서,상기 유기 발광 소자는,제1전극;제2 전극;상기 제1 전극과 제2 전극의 내측에 개재되는 1층 이상의 유기물층; 및상기 제1 전극과 제2 전극 중 어느 하나 이상의 전극 외측에 배치되는 캡핑층을 포함하며,상기 발광 소자용 화합물은 상기 캡핑층에 함유되는 유기 발광 소자.
- 제21항에 있어서,상기 캡핑층의 두께는 100Å 내지 3000Å 범위내인 유기 발광 소자.
- 제21항에 있어서,상기 캡핑층은 450nm 파장에서의 굴절률이 1.55 이하인 유기 발광 소자.
- 제21항에 있어서,상기 캡핑층은 제1항의 발광 소자용 화합물을 함유하는 제1캡핑층 및 상기 제1캡핑층보다 고굴절인 제2캡핑층을 포함하는 유기 발광 소자.
- 제24항에 있어서,상기 제2캡핑층은 상기 제1캡핑층과 상기 제1 전극 사이에 개재되거나 상기 제1캡핑층과 제2 전극의 사이에 개재되는 유기 발광 소자.
- 제24항에 있어서,상기 제2 캡핑층은 상기 제1캡핑층 및 상기 제1 전극 또는 상기 제1캡핑층 및 제2 전극과 접촉하는 유기 발광 소자.
- 제24항에 있어서,상기 제1캡핑층 및 제2 캡핑층을 합친 두께는 100 내지 3000 Å 범위내인 유기 발광 소자.
- 제24항에 있어서,상기 제1캡핑층은 450nm 파장에서의 굴절률이 1.55 이하이며, 상기 제2 캡핑층은 450nm 파장에서의 굴절률이 2.10 이상이며, 450nm 파장에서 상기 제1캡핑층의 굴절률과 제2 캡핑층의 굴절률 차이는 0.2 내지 1.2 범위내인 유기 발광 소자.
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