US20220278285A1 - Compound for organic electric element, organic electric element comprising the same, and electronic device thereof - Google Patents

Compound for organic electric element, organic electric element comprising the same, and electronic device thereof Download PDF

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US20220278285A1
US20220278285A1 US17/346,936 US202117346936A US2022278285A1 US 20220278285 A1 US20220278285 A1 US 20220278285A1 US 202117346936 A US202117346936 A US 202117346936A US 2022278285 A1 US2022278285 A1 US 2022278285A1
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ring
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compound
mmol
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Mi Young Chae
Hye Min CHO
Min Ji JO
Soung Yun MUN
Sun Hee Lee
Nam Geol LEE
Hyung Dong Lee
Dae Hwan OH
Ga Eun Lee
Sang Yong Park
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DukSan Neolux Co Ltd
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DukSan Neolux Co Ltd
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Definitions

  • the present invention relates to compounds for organic electric elements, organic electric elements comprising the same, and electronic devices thereof.
  • an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy of an organic material.
  • An organic electric element utilizing the organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer interposed therebetween.
  • the organic material layer has a multi-layered structure having respectively different materials in order to improve efficiency and stability of an organic electric element, and for example, may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like.
  • Materials used as an organic material layer in an organic electric element may be classified into a light emitting material and a charge transport material, for example, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to its function.
  • the light emitting material may be divided into a high molecular weight type and a low molecular weight type according to its molecular weight, and may also be divided into a fluorescent material derived from excited singlet states of electron and a phosphorescent material derived from excited triplet states of electron according to its light emitting mechanism. Further, the light emitting material may be divided into blue, green, and red light emitting material and yellow and orange light emitting material required for better natural color reproduction according to its light emitting color.
  • a host/dopant system may be used as the light emitting material in order to enhance the color purity and increase the luminous efficiency through energy transfer. This is based on the principle that if a small amount of dopant having a smaller energy band gap than a host forming a light emitting layer is mixed in the light emitting layer, then excitons generated in the light emitting layer are transported to the dopant, thus emitting light with high efficiency. With regard to this, since the wavelength of the host is shifted to the wavelength band of the dopant, light having a desired wavelength can be obtained according the type of the dopant.
  • the power consumption is required more than more as size of display becomes larger and larger in the portable display market. Therefore, the power consumption is a very important factor in the portable display with a limited power source of the battery, and efficiency and life span issue also is solved.
  • Efficiency, life span, driving voltage, and the like are correlated with each other. For example, if efficiency is increased, then driving voltage is relatively lowered, and the crystallization of an organic material due to Joule heating generated during operation is reduced as driving voltage is lowered, as a result of which life span shows a tendency to increase. However, efficiency cannot be maximized only by simply improving the organic material layer. This is because long life span and high efficiency can be simultaneously achieved when an optimal combination of energy levels and T 1 values, inherent material properties (mobility, interfacial properties, etc.), and the like among the respective layers included in the organic material layer is given.
  • an emission-auxiliary layer (multi-layered hole transport layer) must be present between the hole transport layer and the light emitting layer in order to solve the problems of luminescence in the hole transport layer and the driving voltage, and it is necessary to develop different emission-auxiliary layers according to respective light emitting layers.
  • an electron is transferred from an electron transport layer to a light emitting layer and a hole is transferred from a hole transport layer to the light emitting layer, as a result, an exciton is formed by the recombination of the electron and hole within the light emitting layer.
  • material used in a hole transport layer has a low T1 value because the material should have a low HOMO value.
  • the exciton generated in the light emitting layer is transferred to the hole transport layer and it causes charge unbalance in the light emitting layer, thereby emitting light at the interface of the hole transport layer.
  • the emission-auxiliary layer having a HOMO level between the HOMO energy level of the hole transporting layer and the HOMO energy level of the light emitting layer, a high T1 energy value and a hole mobility within a suitable driving voltage range (within a driving voltage range of blue element of a full device).
  • materials forming the organic material layer in the element such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, an emission-auxiliary layer material, etc. should be prerequisite to support by a stable and efficient material, and in particular, it is strongly required to develop material of host of a light emitting layer, a hole transport layer and an emission-auxiliary layer.
  • the present invention is to provide a compound lowering a driving voltage, improving luminous efficiency, color purity, stability and lifetime of the element, an organic electric element comprising the same, and an electronic device thereof.
  • the present invention provides the compound represented by the following formula 1.
  • the present invention provides the compound represented by the following Formula A.
  • the present invention provides an organic electric element using the compound represented by formula 1 or A above and an electronic device thereof.
  • a driving voltage can be lowered and the luminous efficiency, color purity, stability and lifetime of the element can be largely improved.
  • the FIGURE illustrates an example of an organic electroluminescent element according to the present invention: 100 is organic electric element, 110 is substrate, 120 is first electrode, 130 is hole injection layer, 140 is hole transport layer, 141 is buffer layer, 150 is light emitting layer, 151 is emission-auxiliary layer, 160 is electron transport layer, 170 is electron injection layer, and 180 is second electrode.
  • aryl group or arylene group as used herein has, but not limited to, 6 to 60 carbon atoms.
  • the aryl group or arylene group in the present invention may comprise a monocyclic ring, ring assemblies, a fused polycyclic system, spiro compounds and the like.
  • heterocyclic group means a non-aromatic ring as well as an aromatic ring like “heteroaryl group” or “heteroarylene group”, and unless otherwise stated, it means a ring comprising one or more heteroatoms and having 2 to 60 carbon atoms, but not limited thereto.
  • hetero atom as used herein represents N, O, S, P or Si
  • the heterocyclic group means a monocyclic form, ring assemblies, a fused polycyclic system or a spiro compound comprising heteroatom(s).
  • heterocyclic group means a ring comprising a heteroatom like N, O, S, P, Si or the like instead of carbon consisting of a ring, it comprises a non-aromatic ring as well as an aromatic ring like “heteroaryl group” or “heteroarylene group” and the compound comprising the heteroatom group like SO 2 , P ⁇ O or the like instead of carbon consisting of a ring such as the following compound.
  • fluorenyl group or “fluorenylene group” as used herein means univalent or bivalent functional group in which R, R′ and R′′ are all hydrogen in the following structure
  • substituted fluorenyl group or “substituted fluorenylene group” means that at least any one of R, R′ and R′′ is a substituent other than hydrogen, and it comprises spiro compound formed by linking R and R′ together with the carbon bonded to them.
  • spiro compound as used herein has, a spiro union which means union having one atom as the only common member of two rings.
  • the common atom is designated as ‘spiro atom’.
  • the compounds are defined as ‘monospiro-’, ‘dispiro-’ or ‘trispiro-’ depending on the number of spiro atoms in one compound.
  • a ‘group name’ corresponding to an aryl group, an arylene group, a heterocyclic group, and the like exemplified for each symbol and its substituent may be written in the name of functional group reflecting the valence, and may also be described under the name of a parent compound.
  • phenanthrene which is a kind of aryl group
  • it may be described by distinguishing valence such as ‘phenanthryl (group)’ when it is ‘monovalent group’, and as ‘phenanthrylene (group)’ when it is ‘divalent group’, and it may also be described as apparent compound name, ‘phenanthrene’, regardless of its valence.
  • pyrimidine it may be described as ‘pyrimidine’ regardless of its valence, and it may also be described as the name of corresponding functional group such as pyrimidinyl (group) when it is ‘monovalent group’, and as ‘pyrimidylene (group)’ when it is ‘divalent group’.
  • the substituent R 1 is absent when a is an integer of zero, the sole R 1 is bonded to any one of the carbon atoms constituting the benzene ring when a is an integer of 1, when a is an integer of 2 or 3, the substituent R 1 s may be bonded as follows and the substituents R 1 s may be the same or different each other, and the substituent R 1 s may be bonded to the carbon of the benzene ring in a similar manner when a is an integer of 4 to 6.
  • the indication of the hydrogen bonded to the carbon which forms the benzene ring is omitted.
  • the FIGURE illustrates an organic electric element according to an embodiment of the present invention.
  • an organic electric element 100 includes a first electrode 120 formed on a substrate 110 , a second electrode 180 , and an organic material layer formed between the first electrode 120 and the second electrode 180 and comprising the compound of the present invention.
  • the first electrode 120 may be an anode (positive electrode)
  • the second electrode 180 may be a cathode (negative electrode).
  • the first electrode may be a cathode
  • the second electrode may be an anode.
  • the organic material layer may include a hole injection layer 130 , a hole transport layer 140 , a light emitting layer 150 , an electron transport layer 160 , and an electron injection layer 170 formed in sequence on the first electrode 120 .
  • at least one layer of the organic material layer may be omitted, or the organic material layer may further include a hole blocking layer, an electron blocking layer, an emission-auxiliary layer 151 , an electron transport auxiliary layer, a buffer layer 141 , etc., and the electron transport layer 160 or the like may serve as the hole blocking layer.
  • the organic electric element according to an embodiment of the present invention may further include at least a protective layer or a layer for improving luminous efficiency.
  • the layer for improving luminous efficiency may be formed on a surface that does not face the organic material layer of both surfaces of the first electrode or the second electrode.
  • the inventive compound employed in the organic material layer may be used as a material of a hole injection layer 130 , a hole transport layer 140 , an emission-auxiliary layer 151 , an electron transport auxiliary layer, an electron transport layer 160 , an electron injection layer 170 and the like, as a host or a dopant material of a light emitting layer 150 , or as a material of a layer for improving luminous efficiency.
  • the compound according to Formula 1 of the present invention may be used as material of the light emitting layer 150 , preferably, as host material of the light emitting layer 150 , a mixture of the compound according to Formula 1 of the present invention and the compound according to Formula 12 of the present invention may be used as host material, and the compound according to Formula 20 of the present invention may be used as material of a hole transport layer or an emission-auxiliary layer.
  • the compound represented by Formula 21 or 22 of the present invention may be used as material of a hole transport layer, and the compound represented by Formula 23 or 24 of the present invention may be used as material of an emission-auxiliary layer.
  • the compound represented by Formula A of the present invention may be used as material of an emission-auxiliary layer, specially, a green emission-auxiliary layer.
  • energy level and T 1 value between the respective layers of the organic material layer, inherent material properties (mobility, interfacial properties, etc.) and the like can be optimized by using as a host material of a light emitting layer a single compound represented by the Formula 1 or a mixture of the compound represented by the Formula 1 and the compound represented by the Formula 12, by using these compounds as a light-emitting layer material and simultaneously using the compound according to the formula 20 as a hole transport layer or an emission-auxiliary layer, and thus it is possible to simultaneously improve the life span and efficiency of the organic electric element.
  • the organic electric element according to an embodiment of the present invention may be manufactured using various deposition methods.
  • the organic electric element according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) method or CVD (chemical vapor deposition) method.
  • the organic electric element may be manufactured by depositing a metal, a conductive metal oxide, or a mixture thereof on the substrate to form the anode 120 , forming the organic material layer including the hole injection layer 130 , the hole transport layer 140 , the light emitting layer 150 , the electron transport layer 160 , and the electron injection layer 170 thereon, and then depositing a material, which can be used as the cathode 180 , thereon.
  • an emitting auxiliary layer 151 may be formed between a hole transport layer 140 and a light emitting layer 150
  • an electron transport auxiliary layer may be formed between a light emitting layer 150 and an electron transport layer 160 .
  • the organic material layer may be manufactured in such a manner that a smaller number of layers are formed using various polymer materials by a soluble process or solvent process, for example, spin coating, nozzle printing, inkjet printing, slot coating, dip coating, roll-to-roll, doctor blading, screen printing, or thermal transfer, instead of deposition. Since the organic material layer according to the present invention may be formed in various ways, the scope of protection of the present invention is not limited by a method of forming the organic material layer.
  • the organic electric element according to an embodiment of the present invention may be of a top emission type, a bottom emission type, or a dual emission type depending on the material used.
  • the organic electric element may be any one of an organic light emitting diode, an organic solar cell, an organic photo conductor, an organic transistor, and an element for monochromatic or white illumination.
  • the electronic device including a display device which includes the above described organic electric element, and a control unit for controlling the display device.
  • the electronic device may be a wired/wireless communication terminal which is currently used or will be used in the future, and covers all kinds of electronic devices including a mobile communication terminal such as a cellular phone, a personal digital assistant (PDA), an electronic dictionary, a point-to-multipoint (PMP), a remote controller, a navigation unit, a game player, various kinds of TVs, and various kinds of computers.
  • a mobile communication terminal such as a cellular phone, a personal digital assistant (PDA), an electronic dictionary, a point-to-multipoint (PMP), a remote controller, a navigation unit, a game player, various kinds of TVs, and various kinds of computers.
  • PDA personal digital assistant
  • PMP point-to-multipoint
  • X 1 and X 2 are each independently O or S, provided that X 1 and X 2 are different from each other. That is, one of X 1 and X 2 is O and the other is S.
  • Ar 1 to Ar 3 are each independently selected from the group consisting of a C 6 -C 60 aryl group, a fluorenyl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring, a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring, a C 1 -C 50 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 30 alkoxyl group, a C 6 -C 30 aryloxy group and -L′-N(R a )(R b ).
  • Ar 1 to Ar 3 may be preferably a C 6 -C 30 or a C 6 -C 20 aryl group, more preferably a C 6 -C 18 aryl group, for example, phenyl, biphenyl, naphthyl, phenanthryl, terphenyl or the like.
  • Ar 1 to Ar 3 When Ar 1 to Ar 3 are each a heterocyclic group, Ar 1 to Ar 3 may be preferably a C 2 -C 30 or a C 2 -C 20 heterocyclic group, more preferably a C 2 -C 18 heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimidido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine and the like.
  • Ar 1 to Ar 3 When Ar 1 to Ar 3 are each a fluorenyl group, Ar 1 to Ar 3 may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene or the like.
  • Ar 2 and Ar 3 may be preferably a C 6 -C 50 or a C 6 -C 22 aryl group, more preferably a C 6 -C 18 aryl group, for example, phenyl, biphenyl, naphthyl, phenanthryl, terphenyl or the like.
  • Ar 1 to Ar 3 When Ar 1 to Ar 3 are each a heterocyclic group, Ar 1 to Ar 3 may be preferably a C 2 -C 30 or a C 2 -C 20 heterocyclic group, more preferably a C 2 -C 18 heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimidido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine and the like.
  • Ar 1 to Ar 3 When Ar 1 to Ar 3 are each a fluorenyl group, Ar 2 and Ar 3 may be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene or the like.
  • R 1 to R 4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C 6 -C 60 aryl group, a fluorenyl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring, a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 50 aromatic ring, a C 1 -C 50 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 30 alkoxyl group, a C 6 -C 30 aryloxy group and -L′-N(R a )(R b ), and adjacent groups may be optionally linked to each other to form a C 6 -C 60 aromatic ring, a C 2 -
  • a to d are each an integer of 0 to 3, where each of these is an integer of 2 or more, each of R 1 s, each of R 2 s, each of R 3 s or each of R 4 s is the same or different from each other.
  • R 1 to R 4 When R 1 to R 4 are each an aryl group, R 1 to R 4 may be preferably a C 6 -C 30 or a C 6 -C 20 aryl group, more preferably a C 6 -C 18 aryl group, for example, phenyl, biphenyl, naphthyl, terphenyl or the like.
  • R 1 to R 4 When R 1 to R 4 are each a heterocyclic group, R 1 to R 4 may be preferably a C 2 -C 30 or a C 2 -C 20 heterocyclic group, more preferably a C 2 -C 8 heterocyclic group, for example, triazine, pyrimidine, pyridine, quinazoline or the like.
  • the ring formed by linking between adjacent R 1 s, between adjacent R 2 s, between adjacent R 3 , or between adjacent R 4 may be preferably a C 6 -C 20 aromatic ring group, or a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, more preferably, a C 6 -C 10 aromatic ring group, or a C 2 -C 10 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, for example, benzene ring, naphthalene, phenanthrene, thiophene, benzothiophene, pyridine and the like.
  • an aromatic ring or a heterocycle comprising a benzene ring may be formed together with the benzene ring to which they are attached, preferably a C 6 -C 14 aromatic ring or a C 2 -C 14 heterocycle may be formed.
  • L′ is selected from the group consisting of a single bond, a C 6 -C 60 arylene group, a fluorenylene group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring and a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring.
  • L′ When L′ is an arylene group, L′ may be preferably a C 6 -C 30 or C 6 -C 20 arylene group, more preferably a C 6 -C 18 arylene group, for example, phenylene, biphenyl, naphthalene, terphenyl or the like.
  • R a and R b are each independently selected from the group consisting of hydrogen, a C 6 -C 60 aryl group, a fluorenyl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring and a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring.
  • R a and R b are each an aryl group
  • R a and R b may be preferably a C 6 -C 30 or C 6 -C 20 aryl group, more preferably a C 6 -C 18 aryl group, for example, phenyl, biphenyl, naphthyl, terphenyl or the like.
  • Ar 1 to Ar 3 , R 1 to R 4 , L′, R a , R b , and the ring formed by bonding between neighboring R 1 s to neighboring R 4 s may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a C 1 -C 20 alkylthio group, a C 1 -C 20 alkoxyl group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group,
  • Ar 1 to Ar 3 , R 1 to R 4 , L′, R a , R b , and a ring formed by bonding between neighboring R 1 s to neighboring R 4 s are each an aryl group, an arylene group, an aromatic hydrocarbon, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring (group), a fused ring (group), an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group and the like, each of these may be further substituted with one or more substituents selected from the group consisting of substituents such as deuterium, halogen and the like.
  • the aryl group is preferably a C 6 -C 20 aryl group, more preferably, a C 6 -C 18 aryl group, for example, phenyl, naphthyl, biphenyl, terphenyl, and the like.
  • the heterocyclic group is preferably a C 2 -C 20 heterocyclic group, more preferably, a C 2 -C 12 heterocyclic group, for example, pyrazine, pyrimidine, pyridine, quinazoline, isoindole, carbazole, dibenzothiophene, and the like.
  • the alkyl group is preferably a C 1 -C 10 alkyl group, more preferably, a C 1 -C 4 alkyl group, for example, methyl, t-butyl and the like.
  • Ar 1 to Ar 3 , R 1 to R 4 , L′, R a , R b , and a ring formed by bonding between neighboring R 1 s to R 4 s may be further substituted with the substituents such as F, CN, ethen and the like.
  • Formula 1 may be represented by one of the following Formula 2 to Formula 11.
  • each symbol is as defined for Formula 1.
  • X 1 , X 2 , Ar 1 to Ar 3 , R 1 to R 4 , a, b, c and d are the same as defined for Formula 1.
  • At least one of Ar 1 to Ar 3 may be a substituted or unsubstituted C 6 -C 24 aryl group, more preferably, Ar 1 to Ar 3 may be all a substituted or unsubstituted C 6 -C 12 aryl group, and Ar 2 and Ar 3 may be different from each other.
  • the compound represented by formula 1 may be one of the following compounds, but it is not limited thereto.
  • the present invention provides an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises compound represented by Formula 1.
  • the organic material layer comprises at least one layer of a hole injection layer, a hole transport layer, an emission-auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, preferably, the compound represented by Formula 1 is comprised in the light emitting layer, more preferably, a single compound or compounds of two or more kinds represented by Formula 1 may be used as host material of the light emitting layer.
  • the light emitting layer may further comprise the compound represented by the following Formula 12.
  • Z 1 to Z 4 , Z 13 to Z 16 are independently C(R) or N, Z 5 to Z 12 are independently C, C(R) or N.
  • L 2 is selected from the group consisting of a single bond, a C 6 -C 60 arylene group, a fluorenylene group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring and a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring.
  • L 2 When L 2 is an arylene group, L 2 may be preferably a C 0 -C 30 or C 6 -C 20 arylene group, more preferably a C 6 -C 18 arylene group, for example, phenylene, naphthalene, biphenyl, terphenyl or the like.
  • L 2 When L 2 is a heterocyclic group, L 2 may be preferably a C 2 -C 30 or C 2 -C 20 heterocyclic group, more preferably a C 2 -C 18 heterocyclic group, for example, carbazole, phenylcarbazole or the like.
  • W is N(Ar 5 ), N, O, S, C(R′) or C(R′)(R′′), and W is N or C(R′) when W is combined with L 2 .
  • Ar 4 and Ar 5 are each independently selected from the group consisting of a C 6 -Cao aryl group, a fluorenyl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 50 aliphatic ring, a fused ring group formed by a C 3 -C 50 aliphatic ring with a C 6 -C 60 aromatic ring, a C 1 -C 50 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 2 a alkynyl group, a C 1 -C 30 alkoxyl group, a C 6 -C 30 aryloxy group, -L′-N(R a )(R b ) and a combination thereof.
  • a combination thereof means, for example, a combination of an aryl group and a heterocyclic group, a combination of an aryl group and an aliphatic ring, a combination of a heterocyclic group and an aliphatic ring group, and the like.
  • R, R′ and R′′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C 6 -C 50 aryl group, a fluorenyl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring, a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring, a C 1 -C 60 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 30 alkoxyl group, a C 6 -C 30 aryloxy group and -L′-N(R a )(R b ), adjacent R groups may be optionally linked to each other to form a ring, and R′ and R′′ may be optionally linked
  • the ring formed by linking between adjacent R groups or between R′ and R′′ may be a C 6 -C 60 aromatic ring group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring, or a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring, preferably, a C 6 -C 20 aromatic ring group or a C 2 -C 20 heterocyclic group, more preferably, a C 6 -C 10 aromatic ring group or a C 2 -C 10 heterocyclic group, for example, benzene, naphthalene, phenanthrene, thiophene, benzothiophene, pyridine and the like.
  • L′, R a and R b are the same as defined for Formula 1.
  • L 2 , Ar 4 , Ar 5 , R, R′, R′′, the ring formed by linking between adjacent R groups, and the ring formed by linking between R′ and R′′ may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a C 1 -C 20 alkylthio group, a C 1 -C 20 alkoxyl group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -
  • Formula 12 is represented by one of Formulas 13 to 17.
  • Ar 4 , Ar 5 , Z 1 to Z 16 , L 2 , R and R are the same as defined for Formula 12.
  • At least one of Ar 4 and Ar 5 may be a substituted or unsubstituted C 6 -C 30 aryl group, more preferably, both Ar 4 and Ar 5 are a C 6 -C 30 aryl group.
  • Formula 12 may be represented by Formula 18 or Formula 19.
  • Ar 4 , Z 1 to Z 16 , and L 2 are the same as defined for Formula 12.
  • L 1 is selected from the group consisting of a single bond, a C 6 -C 60 arylene group, a fluorenylene group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring and a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring.
  • L 1 when L 1 is an arylene group, L 1 may be preferably a C 6 -C 30 or C 6 -C 20 arylene group, more preferably a C 6 -C 12 arylene group, for example, phenylene, naphthalene, biphenyl or the like,
  • Y is O, S or N—Ar 6 .
  • R a and R b are each independently selected from the group consisting of deuterium, halogen, a C 6 -C 20 aryl group, a C 6 -C 20 aryl group substituted with deuterium, a fluorenyl group, a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20 cycloalkyl group, a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring, a C 7 -C 20 arylalkyl group and a C 8 -C 20 arylalkenyl group, and adjacent groups may be optionally linked to each other to form a C 6 -C 60 aromatic ring, a C 2 -C 60 heterocyclic group, a C 3 -C 60 aliphatic ring, or a fused ring group formed by a C
  • y is an integer of 0 to 3
  • z is an integer of 0 to 4, where each of these is an integer of 2 or more, each of R a s, each of R b s is the same or different from each other.
  • Ar 6 is selected from the group consisting of a C 6 -C 60 aryl group, a C 6 -C 60 aryl group substituted with deuterium, a fluorenyl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 cycloalkyl group, a fused ring group formed by a C 3 -C 50 aliphatic ring with a C 6 -C 60 aromatic ring, a C 1 -C 60 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 30 alkoxyl group, a C 6 -C 30 aryloxy group, a C 7 -C 20 arylalkyl group and a C 8 -C 20 arylalkenyl group.
  • Ar 6 is selected from the group consisting of a C 6 -C 20 aryl group, a C 6 -C 20 aryl group substituted with deuterium, a fluorenyl group, a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 20 cycloalkyl group, a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring, a C 7 -C 20 arylalkyl group and a C 8 -C 20 arylalkenyl group.
  • the compound represented by formula 12 may be one of the following compounds, but it is not limited thereto.
  • the organic material layer of an organic element according to the present invention comprises a light emitting layer, a hole transport layer formed between the first electrode and the light emitting layer, and an emission-auxiliary layer formed between the light emitting layer and the hole transport layer, the light emitting layer comprises the compound represented by Formula 1, and the hole transport layer or the emission-auxiliary layer comprises the compound represented by Formula 20.
  • Ar 4 and Ar 5 are each independently selected from the group consisting of a C 6 -C 50 aryl group, a fluorenyl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring, a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring, a C 1 -C 50 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 30 alkoxyl group, a C 6 -C 30 aryloxy group and -L′-N(R a )(R b ), and Ar 4 and Ar 5 may be combined with each other to form a ring.
  • Ar 6 is selected from the group consisting of a C 6 -C 60 aryl group, a fluorenyl group, and a C 2 -C 50 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; or Ar 6 is selected from the group consisting of the following Formulas 1-a to 1-c.
  • Ar 9 to Ar 11 are each independently selected from the group consisting of a C 6 -C 50 aryl group, a fluorenyl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring, a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring, a C 1 -C 50 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 30 alkoxyl group, a C 6 -C 30 aryloxy group and -L′-N(R a )(R b ).
  • L 5 is selected from the group consisting of a C 6 -C 60 arylene group, a fluorenylene group, and a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring and a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring.
  • L 6 is selected from the group consisting of a single bond, a C 6 -C 60 arylene group, a fluorenylene group, and a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring and a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 50 aromatic ring.
  • R 6 to R 9 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C 6 -C 60 aryl group, a fluorenyl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring, a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 50 aromatic ring, a C 1 -C 50 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 30 alkoxyl group, a C 6 -C 30 aryloxy group and -L′-N(R a )(R b ).
  • h, i and g are each an integer of 0 to 4
  • j is an integer of 0 to 3 where each of these is an integer of 2 or more, a plurality of R 6 s, a plurality of R 7 s, a plurality of R 8 s, a plurality of R 9 s are the same as or different from each other.
  • adjacent R 6 groups, adjacent R 7 groups, adjacent R 8 groups, or adjacent R 9 groups may be linked to each other to form a ring.
  • the ring formed by linking between adjacent groups may be a C 6 -C 60 aromatic ring group, a C 2 -C 50 heterocyclic group, a C 3 -C 50 aliphatic ring, or a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring.
  • L′, R a and R b are the same as defined for Formula 1.
  • Ar 4 to Ar 6 , Ar 9 to Ar 11 , R 6 to R 9 , L 5 , L 6 , and the ring formed by bonding between neighboring groups may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a C 1 -C 20 alkylthio group, a C 1 -C 20 alkoxyl group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 al
  • the light emitting layer may further comprise the compound represented by Formula 12.
  • the hole transport layer comprises the compound represented by the following Formula 21 or Formula 22 and the emission-auxiliary layer comprises the compound represented by the following Formula 23 or Formula 24.
  • Ar 4 , Ar 5 , Ar 9 to Ar 11 , h, i, g, j, L 5 , L 6 , R 6 to R 9 are the same as defined above
  • Ar 7 is selected from the group consisting of a C 6 -C 60 aryl group, a fluorenyl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, and a C 3 -C 60 aliphatic ring.
  • at least one of Ar 4 , Ar 5 , Ar 10 and Ar 11 may be represented by Formula 24-1.
  • R a′ , R b′ and R c′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 6 -C 20 aryl group, a fluorenyl group, a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C 3 -C 20 cycloalkyl group, and a fused ring group formed by a C 3 -C 50 aliphatic ring with a C 6 -C 60 aromatic ring, and adjacent groups may be optionally linked to each other to form a ring.
  • the ring may be a C 6 -C 60 aromatic ring group, a C 2 -C 60 heterocyclic group, a C 3 -C 60 aliphatic ring, or a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring.
  • I′, m′ and n′ are each an integer of 0 to 4, where each of these is an integer of 2 or more, a plural of R a′ s, a plural of R b′ s or a plural of R c′ s are each the same or different from each other.
  • Ar 1′ is selected from the group consisting of a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 6 -C 20 aryl group, a fluorenyl group, a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C 3 -C 20 cycloalkyl group, and a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring.
  • R a′ , R b′ , R c′ , Ar 1′ and the ring formed by bonding between neighboring may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a C 1 -C 20 alkylthio group, a C 1 -C 20 alkoxyl group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C
  • Ar 1′ and L 5 are each independently a C 6 -C 60 arylene group, for example, phenyl, biphenyl, o-terphenyl, m-terphenyl, p-terphenyl or naphthalene.
  • Formula 24 may be represented by the following Formula A.
  • R a′ , R b′ , R c′ , Ar 1′ , l′, m′ and n′ are the same as defined for Formula 24-1, Ar 2′ is the same as defined for Ar 11 in Formula 24, Ar 3′ is the same as defined for Ar 4 in Formula 24, Ar 4 , is the same as defined for Ar 5 in Formula 24, and a′ is an integer of 1 to 3. That is, in Formula A, each of symbols may be defined as follows.
  • R a′ , R b′ and R c′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 6 -C 20 aryl group, a fluorenyl group, a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C 3 -C 20 cycloalkyl group, and a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 50 aromatic ring, and adjacent groups may be optionally linked to each other to form a ring.
  • the ring may be a C 6 -C 60 aromatic ring group, a C 2 -C 50 heterocyclic group, a C 3 -C 50 aliphatic ring, or a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring.
  • l′, m′ and n′ are each an integer of 0 to 4, where each of these is an integer of 2 or more, a plural of R a′ s, a plural of R b′ s or a plural of R c′ s are each the same or different from each other.
  • Ar 1′ is selected from the group consisting of a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 6 -C 20 aryl group, a fluorenyl group, a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C 3 -C 20 cycloalkyl group, and a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring.
  • Ar 1′ is an aryl group
  • Ar 1′ may be preferably a C 6 -C 18 aryl group, more preferably a C 6 -C 12 aryl group, for example, phenyl, biphenyl, terphenyl, naphthyl or the like.
  • Ar 2′ , Ar 3′ and Ar 4′ are each independently selected from the group consisting of a C 6 -C 60 aryl group, a fluorenyl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring, a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring, a C 1 -C 60 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 30 alkoxyl group, a C 6 -C 30 aryloxy group and -L′-N(R a )(R b ), Ar 4 and Ar 5 may be linked to each other to form a ring.
  • Ar 4 and Ar 5 may be linked to each other to form
  • Ar 2′ is an aryl group
  • Ar 2′ may be preferably a C 6 -C 30 aryl group, more preferably a C 6 -C 18 aryl group, for example, phenyl, naphthyl, biphenyl, terphenyl or the like.
  • Ar 2′ is a heterocyclic group
  • Ar 2′ may be preferably a C 2 -C 30 heterocyclic group, more preferably a C 2 -C 16 heterocyclic group, for example, dibenzofuran, dibenzothiophene and the like.
  • Ar 2′ is a fluorenyl group
  • Ar 2′ may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9′-spirobifluorene and the like.
  • Ar 3′ and Ar 4′ are each an aryl group
  • Ar 3′ and Ar 4′ may be preferably a C 6 -C 30 aryl group, more preferably a C 6 -C 18 aryl group, for example, phenyl, biphenyl, terphenyl, naphthyl, triphenylene, phenanthrene or the like.
  • Ar 3′ and Ar 4′ are each a heterocyclic group
  • Ar 3′ and Ar 4′ may be preferably a C 2 -C 30 heterocyclic group, more preferably a C 2 -C 12 heterocyclic group, for example, dibenzofuran, dibenzothiophene and the like.
  • Ar 3′ and Ar 4′ are each a fluorenyl group
  • Ar 3′ and Ar 4′ may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9′-spirobifluorene and the like.
  • L′ is selected from the group consisting of a single bond, a C 6 -C 60 arylene group, a fluorenylene group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring and a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring,
  • R a and R b are each independently selected from the group consisting of hydrogen, a C 6 -C 60 aryl group, a fluorenyl group, a C 2 -C 60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C 3 -C 60 aliphatic ring and a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring.
  • R a′ , R b′ , R c′ , R a , R b , Ar 1′ to Ar 4′ , L′ and a ring formed by bonding between neighboring groups may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a C 1 -C 20 alkylthio group, a C 1 -C 20 alkoxyl group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl
  • Formula A may be represented by one of Formula B to Formula D.
  • R a′ , R b′ , R c′ , l′, m′, n′, Ar 1′ to Ar 4′ are the same as defined for Formula A.
  • Formula A may be represented by one of Formula E to Formula G.
  • R a′ , R b′ , R c′ , l′, m′, n′, Ar 1′ to Ar 4′ are the same as defined for Formula A.
  • Formula A may be represented by one of Formula H to Formula K.
  • R a′ , R b′ , R c′ , l′, m′, n′, Ar 1′ to Ar 3′ are the same as defined for Formula A.
  • X is independently O, S or C(R′)(R′′),
  • R d′ , R e′ , R′ and R′′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 6 -C 20 aryl group, a fluorenyl group, a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C 3 -C 20 cycloalkyl group, and a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring, and adjacent groups may be optionally linked to each other to form a ring.
  • the ring may be a C 6 -C 60 aromatic ring group, a C 2 -C 60 heterocyclic group, a C 3 -C 60 aliphatic ring, or a fused ring group formed by a C 3 -C 60 aliphatic ring with a C 6 -C 60 aromatic ring, and when R′ group and R′′ group are linked to each other to form a ring, a spiro compound may be formed together with C to which they are attached.
  • o′ is independently an integer of 0 to 3
  • p′ is independently an integer of 0 to 4, where o′ is an integer of 2 or more, a plural of R d′ s are each the same or different from each other, where p′ is an integer of 2 or more, a plural of R e′ s are each the same or different from each other.
  • R d′ , R e′ , R′, R′′ and the ring formed by bonding between neighboring groups may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a C 1 -C 20 alkylthio group, a C 1 -C 20 alkoxyl group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 6 -
  • Formula A may be represented by one of Formula L to Formula O.
  • R a′ , R b′ , R c′ , l′, m′, n′, Ar 3′ and Ar 4′ are the same as defined for Formula A.
  • R e′ , R f′ , R g′ , R h′ and R l′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 6 -C 20 aryl group, a fluorenyl group, a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C 3 -C 20 cycloalkyl group, and a fused ring group formed by a C 3 -C 50 aliphatic ring with a C 6 -C 60 aromatic ring, and adjacent groups may be optionally linked to each other to form a ring.
  • the ring may be a C 6 -C 60 aromatic ring group, a C 2 -C 60 heterocyclic group, a C 3 -C 50 aliphatic ring, or a fused ring group formed by a C 3 -C 50 aliphatic ring with a C 6 -C 60 aromatic ring.
  • each of R e′ s, each of R f′ s, each of R g′ s, each of R h′ s, and each of R l′ s is each the same or different from each other.
  • b′ is an integer of 0 to 3.
  • R e′ , R f′ , R g′ , R h′ , R l′ and the ring formed by bonding between neighboring groups may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group, a C 1 -C 20 alkylthio group, a C 1 -C 20 alkoxyl group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alky
  • the compound represented by formula 20 may be one of the following compounds, but it is not limited thereto.
  • the compound represented by formula A may be one of the following compounds, but it is not limited thereto.
  • the present invention provides an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a single compound or compounds of two or more kinds represented by Formula 1.
  • the present invention provides an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a single compound or compounds of two or more kinds represented by Formula A.
  • the organic material layer comprises at least one layer of a hole injection layer, a hole transport layer, an emission-auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, and preferably, the compound represented by Formula 1 may be comprised in a light emitting layer and the compound represented by Formula A may be comprised in an emission-auxiliary layer, in particular, a green emission-auxiliary layer.
  • the present invention provides an electronic device comprising a display device comprising the organic electric element, and a control unit for driving the display device, wherein the organic electric element comprises the compound represented by Formula 1 or A.
  • the compound represented by Formula according to the present invention can be synthesized by reacting Sub 1 with Sub 2.
  • Sub 1 of the Reaction Scheme 1 can be synthesized according to the reaction route of the following Reaction Scheme 2, but there is no limitation thereto.
  • the compound belonging to Sub 1 may be, but not limited to, the following compounds, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub 1.
  • Sub 2 of the Reaction Scheme 1 can be synthesized according to the reaction route of the following Reaction Scheme 3, but there is no limitation thereto.
  • the compound belonging to Sub 2 may be, but not limited to, the following compounds, and Table 2 shows FD-MS values of compounds belonging to Sub 2.
  • the compound represented by Formula 12 according to the present invention can be synthesized by reacting Sub with Sub 4-1, but there is no limitation thereto.
  • the compound represented by Formula 20 according to the present invention can be synthesized as follows, but is not limited thereto.
  • N-(3-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine (10.6 g, 20 mmol), Pd 2 (dba) 3 (0.5 g, 0.6 mmol), P(t-Bu) 3 (0.2 g, 2 mmol), t-BuONa (5.8 g, mmol) and toluene (300 mL) were added to N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine (7.5 g, 20 mmol), and then 12.9 g (yield: 78%) of the product was obtained by the same method as in synthesis of 14-34.
  • the compound represented by Formula A according to the present invention can be synthesized by reacting Sub a with Sub b, but there is no limitation thereto.
  • the example of the compound belonging to Sub a may be, but not limited to, the following compounds, and Table 5 shows ED-MS values of the following compounds.
  • Sub b of the Reaction Scheme 5 can be synthesized according to the reaction route of the following Reaction Scheme 5-2, but there is no limitation thereto.
  • Example of the compounds belonging to Sub b may be, but not limited to, the following compounds, and Table 6 shows the FD-MS values of the following compounds.
  • the concentrate was dissolved in toluene and filtered with a silica gel filter. After concentrating the filtered solution, the concentrate was recrystallized with toluene and acetone to obtain G-3 (17.0 g, 89%) of the product.
  • the concentrate was dissolved in toluene and filtered with a silica gel filter. After concentrating the filtered solution, the concentrate was recrystallized with toluene and acetone to obtain G-29 (15.20 g, 86%) of the product.
  • the concentrate was dissolved in toluene and filtered with a silica gel filter. After concentrating the filtered solution, the concentrate was recrystallized with toluene and acetone to obtain G-81 (13.99 g, 82%) of the product.
  • the concentrate was dissolved in toluene and filtered with a silica gel filter. After concentrating the filtered solution, the concentrate was recrystallized with toluene and acetone to obtain G-88 (19.47 g, 82%) of the product.
  • the concentrate was dissolved in toluene and filtered with a silica gel filter. After concentrating the filtered solution, the concentrate was recrystallized with toluene and acetone to obtain G-137 (16.24 g, 81%) of the product.
  • the concentrate was dissolved in toluene and filtered with a silica gel filter. After concentrating the filtered solution, the concentrate was recrystallized with toluene and acetone to obtain G-168 (16.92 g, 83%) of the product.
  • N 1 -(naphthalen-2-yl)-N 4 ,N 4 -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N 1 -phenylbenzene-1,4-diamine (hereinafter, “2-TNATA”) was vacuum-deposited on the ITO layer formed on a glass substrate to form a hole injection layer with a thickness of nm.
  • NPD 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
  • a light emitting layer with a thickness of 30 nm was vacuum-deposited on the hole transport layer by using compound 1-1 of the present invention as a host material and tris(2-phenylpyridine)-iridium (hereinafter, “Ir(ppy) 3 ”) as a dopant material in a weight ratio of 95:5.
  • BAlq (1,1′-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum
  • Alq 3 tris-(8-hydroxyquinoline)aluminum
  • LiF was deposited with a thickness of 0.2 nm on the electron transport layer to form an electron injection layer
  • Al was deposited with a thickness of nm on the electron injection layer to form a cathode.
  • the OLED was fabricated in the same manner as described in Example 1 except that compounds of the present invention described in Table 5 instead of the compound 1-1 of the present invention was used as host material of a light emitting layer.
  • the OLEDs were fabricated in the same manner as described in Example 1 except that one of the comparative compounds 1 to 3 instead of compound 1-1 of the present invention was used as host material of a light emitting layer.
  • Electroluminescence (EL) characteristics were measured with PR-650 (Photoresearch) by applying a forward bias DC voltage to the OLEDs prepared in Examples 1 to 15 of the present invention and Comparative Examples 1 to 3. And, the T95 life time was measured using a life time measuring apparatus manufactured by Mcscience Inc. at reference brightness of 5000 cd/m 2 . The measurement results are shown in Tables 8 below.
  • the OLED was fabricated in the same manner as described in Example 1 except that a mixture of the compound represented by Formula 1 and the compound represented by Formula 12 of the present invention described in Table 6 instead of compound 1-1 of the present invention was used as host material of a light emitting layer.
  • the OLEDs were fabricated in the same manner as described in Example 1 except that a mixture of comparative compound 2 and compound 5-27 of the present invention (Comparative Example 4), or a mixture of comparative compound 3 and compound 5-27 of the present invention instead of compound 1-1 of the present invention was used as host material of a light emitting layer.
  • Electroluminescence (EL) characteristics were measured with PR-650 (Photoresearch) by applying a forward bias DC voltage to the OLEDs prepared in Examples 16 to 55 of the present invention and Comparative Examples 4 and 5. And, the T95 life time was measured using a life time measuring apparatus manufactured by Mcscience Inc. at reference brightness of 5000 cd/m 2 . The measurement results are shown in Tables 9 below.
  • compound 14-69 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form an emission-auxiliary layer, and a light emitting layer with a thickness of 30 nm was vacuum-deposited on the hole transport layer by using a mixture of compound 1-1(the first host) and compound 5-27 (the second host) of the present invention in the ratio of 6:4 as a host material and Ir(ppy) 3 ) as a dopant material in a weight ratio of 95:5.
  • BAlq was vacuum-deposited with a thickness of 10 nm on the light emitting layer to form a hole blocking layer
  • Alq 3 was vacuum-deposited with a thickness of 40 nm on the hole blocking layer to form an electron transport layer.
  • LiF was deposited with a thickness of 0.2 nm on the electron transport layer to form an electron injection layer
  • Al was deposited with a thickness of 150 nm on the electron injection layer to form a cathode.
  • the OLEDs were fabricated in the same manner as described in Example 56 except that the compounds of the present invention described in the following Table 7 were used as an emission-auxiliary layer material and the first host material.
  • the OLEDs were fabricated in the same manner as described in Example 56 except that Comparative compound 2 or 3 was used as the first host material.
  • Electroluminescence (EL) characteristics were measured with a PR-650 (Photoresearch) by applying a forward bias DC voltage to the OLEDs prepared in Examples 56 to 73 of the present invention and Comparative Examples 6 and 7. And, the T95 life time was measured using a life time measuring apparatus manufactured by Mcscience Inc. at reference brightness of 5000 cd/m 2 . The measurement results are shown in Tables 10 below.
  • the compound 14-69 of the present invention was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 60 nm.
  • the compound 14-72 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form an emission-auxiliary layer and a light emitting layer with a thickness of 30 nm was vacuum-deposited on the hole transport layer by using a mixture of the compound 1-1(the first host) and the compound 5-27(the second host) of the present invention at 6:4 as a host material and Ir(ppy) 3 ) as a dopant material in a weight ratio of 95:5.
  • BAlq was vacuum-deposited with a thickness of 10 nm on the light emitting layer to form a hole blocking layer
  • Alq 3 was vacuum-deposited with a thickness of 40 nm on the hole blocking layer to form an electron transport layer.
  • LiF was deposited with a thickness of 0.2 nm on the electron transport layer to form an electron injection layer
  • Al was deposited with a thickness of 150 nm on the electron injection layer to form a cathode.
  • the OLEDs were fabricated in the same manner as described in Example 74 except that the compounds of the present invention described in the following Table 8 were used as an emission-auxiliary layer material and the first host material.
  • Electroluminescence (EL) characteristics were measured with a PR-650 (Photoresearch) by applying a forward bias DC voltage to the OLEDs prepared in Examples 74 to 85 of the present invention. And, the T95 life time was measured using a life time measuring apparatus manufactured by Mcscience Inc. at reference brightness of 5000 cd/m 2 . The measurement results are shown in Tables 11 below.
  • Comparative Compound 2 When comparing Comparative Compounds 2 and 3, Comparative Compound 2 is different in that the heteroatom of both heterocycles attached to the triazine is S, while in case of Comparative Compound 3, the heteroatom is O. From Table 9 above, it can be seen that when heteroatoms S are introduced into both heterocycles, the LUMO value is highest (comparative compound 2), and when O is introduced, the LUMO value is lowest (comparative compound 3), the LUMO value is located in the middle when S as a heteroatom is introduced into one heterocycle and O is introduced into the other heterocycle as the compound of the present invention.
  • the compound of the present invention in which the LUMO level is located in the middle of the LUMO level of the comparative compounds is used as a phosphorescent host material, it has an appropriate LUMO level for electron transfer, so the biased electron transfer characteristics of Comparative Compound 2 and Comparative Compound 3 can be complemented. Therefore, when the compound of the present invention is used as a phosphorescent host material, the charge balance in the light-emitting layer increases, so that the luminous efficiency and lifetime of the organic electroluminescent device are improved.
  • Example 5 the device result of Example 5 in which 1-dibenzofuran is substituted in triazine is better than Example 1 in which 4-dibenzofuran is substituted in triazine, and the electrical properties of the device of Example 7 in which a substituent is attached at 2-position in benzene of 1-dibenzofuran instead of 4-position are improved.
  • BAlq was vacuum-deposited with a thickness of 10 nm on the light emitting layer to form a hole blocking layer
  • Alq 3 was vacuum-deposited with a thickness of 40 nm on the hole blocking layer to form an electron transport layer.
  • LiF was deposited with a thickness of 0.2 nm on the electron transport layer to form an electron injection layer
  • Al was deposited with a thickness of 150 nm on the electron injection layer to form a cathode.
  • the OLEDs were fabricated in the same manner as described in Example 86 except that the compounds of the present invention described in the following Table 12, instead of compound G-1 of the present invention, were used as an emission-auxiliary layer material.
  • the OLED was fabricated in the same manner as described in Example 86 except that an emission-auxiliary layer was not formed.
  • the OLEDs were fabricated in the same manner as described in Example 86 except that the following Comparative compounds ref 1 to ref 4, respectively, instead of compound P-1 of the present invention, were used as an emission-auxiliary layer material.
  • Electroluminescence (EL) characteristics were measured with PR-650 (Photoresearch) by applying a forward bias DC voltage to the OLEDs prepared in Examples 86 to 116 of the present invention and Comparative Examples 12 to 16. And, the T95 life time was measured using a life time measuring apparatus manufactured by Mcscience Inc. at reference brightness of 5000 cd/m 2 . The measurement results are shown in Tables 12 below.
  • Ref 1, Ref 3 and Ref 4 differ in the substituents connected to the nitrogen atom of the amine group in the NPB type.
  • a phenyl derivative (biphenyl) is attached to the nitrogen atom of the amine group in Ref 1
  • diphenyl fluorene is attached to the nitrogen atom in Ref 3 and Ref 4.
  • Ref 4 contains one additional amine group and carbazole is bound to the additional amine group, compared to Ref 2. Looking at the device characteristics of Comparative Example 14 and 16 using these compounds as material of an emission-auxiliary layer, it can be seen that efficiency and lifetime are similar, but the driving voltage is better in Comparative Example 14.
  • Example 90 and 97 showed better values than Example 86, wherein a compound (G-27 or G-52) substituted with dibenzofuran or fluorene containing a hetero atom is used in Examples 90 and 97 and Compound G-1 in which a simple phenyl group was substituted with a substituent of an amine group was used as material of an emission-auxiliary layer in Example 86, and the device results of Examples 91 showed better values than Examples 90 and 97, wherein a compound G-29 in which fluorene and dibenzofuran are linked to one nitrogen atom of the amine group is used in Example 91.
  • Example 100 the device results of Example 100 are further improved than Example 105, wherein fluorene-substituted compound G-101 at a nitrogen atom connected to diphenylfluorene is used as material of an emission-auxiliary layer in Example 105, and compound G-66 in which fluorene is substituted at a nitrogen atom of another amine group other than the nitrogen atom connected to diphenylfluorene is used as material of an emission-auxiliary layer in Example 100.
  • Example 86 the device results of Example 86 are further improved than Example 102 when two amine groups of the compound of the present invention are linked to each other through a phenyl linker, wherein a compound G-1 in which two amine groups are linked to the linker phenyl in a meta position is used as material of an emission-auxiliary layer in Example 86 and compound G-74 in which two amine groups are para-linked to phenyl is used as material of an emission-auxiliary layer in Example 102.

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Abstract

Provided are a compound represented by Formula 24, an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode and comprising the compound of Formula 24, and an electronic device thereof, the element and device having improved driving voltage, luminous efficiency and life time from the employment of the compound.

Description

    CROSS-REFERENCE TO RELATED APPLICATION
  • This patent application is a Divisional Application of U.S. patent application Ser. No. 16/652,383, filed on Mar. 30, 2020, which is a 371 of International Patent Application No. PCT/KR2018/009503, filed on Aug. 20, 2018, and claims priority from and the benefit under 35 U.S.C. § 119 to § 121, and § 365 of Korean Patent Application No. 10-2017-0127537, filed on Sep. 29, 2017, Korean Patent Application No. 10-2018-0039162, filed on Apr. 4, 2018, Korean Patent Application No. 10-2018-0072472, filed on Jun. 25, 2018, which are hereby incorporated by reference for all purposes as if fully set forth herein. Further, this application claims the benefit of priority in countries other than U.S., which is hereby incorporated by reference herein.
    • BACKGROUND Technical Field
  • The present invention relates to compounds for organic electric elements, organic electric elements comprising the same, and electronic devices thereof.
    • Background Art
  • In general, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy of an organic material. An organic electric element utilizing the organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer interposed therebetween. In many cases, the organic material layer has a multi-layered structure having respectively different materials in order to improve efficiency and stability of an organic electric element, and for example, may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like.
  • Materials used as an organic material layer in an organic electric element may be classified into a light emitting material and a charge transport material, for example, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to its function.
  • Further, the light emitting material may be divided into a high molecular weight type and a low molecular weight type according to its molecular weight, and may also be divided into a fluorescent material derived from excited singlet states of electron and a phosphorescent material derived from excited triplet states of electron according to its light emitting mechanism. Further, the light emitting material may be divided into blue, green, and red light emitting material and yellow and orange light emitting material required for better natural color reproduction according to its light emitting color.
  • Meanwhile, when only one material is used as a light emitting material, there occur problems of shift of a maximum luminescence wavelength to a longer wavelength due to intermolecular interactions and lowering of the efficiency of a corresponding element due to a deterioration in color purity or a reduction in luminous efficiency. On account of this, a host/dopant system may be used as the light emitting material in order to enhance the color purity and increase the luminous efficiency through energy transfer. This is based on the principle that if a small amount of dopant having a smaller energy band gap than a host forming a light emitting layer is mixed in the light emitting layer, then excitons generated in the light emitting layer are transported to the dopant, thus emitting light with high efficiency. With regard to this, since the wavelength of the host is shifted to the wavelength band of the dopant, light having a desired wavelength can be obtained according the type of the dopant.
  • Currently, the power consumption is required more than more as size of display becomes larger and larger in the portable display market. Therefore, the power consumption is a very important factor in the portable display with a limited power source of the battery, and efficiency and life span issue also is solved.
  • Efficiency, life span, driving voltage, and the like are correlated with each other. For example, if efficiency is increased, then driving voltage is relatively lowered, and the crystallization of an organic material due to Joule heating generated during operation is reduced as driving voltage is lowered, as a result of which life span shows a tendency to increase. However, efficiency cannot be maximized only by simply improving the organic material layer. This is because long life span and high efficiency can be simultaneously achieved when an optimal combination of energy levels and T1 values, inherent material properties (mobility, interfacial properties, etc.), and the like among the respective layers included in the organic material layer is given.
  • In addition, in the recent organic electroluminescent devices, an emission-auxiliary layer (multi-layered hole transport layer) must be present between the hole transport layer and the light emitting layer in order to solve the problems of luminescence in the hole transport layer and the driving voltage, and it is necessary to develop different emission-auxiliary layers according to respective light emitting layers.
  • In general, an electron is transferred from an electron transport layer to a light emitting layer and a hole is transferred from a hole transport layer to the light emitting layer, as a result, an exciton is formed by the recombination of the electron and hole within the light emitting layer. However, material used in a hole transport layer has a low T1 value because the material should have a low HOMO value. As a result, the exciton generated in the light emitting layer is transferred to the hole transport layer and it causes charge unbalance in the light emitting layer, thereby emitting light at the interface of the hole transport layer.
  • When light is emitted from the interface of the hole transporting layer, the color purity and efficiency of the organic electric element are lowered and the lifetime is shortened. Therefore, it is strongly desired to develop materials for the emission-auxiliary layer having a HOMO level between the HOMO energy level of the hole transporting layer and the HOMO energy level of the light emitting layer, a high T1 energy value and a hole mobility within a suitable driving voltage range (within a driving voltage range of blue element of a full device).
  • However, this cannot be achieved simply by the structural properties of the core of the emission-auxiliary layer material. An element having a high efficiency and a long life span can be realized when the characteristics of core and sub-substituents of the emission-auxiliary layer material, the proper combination of the emission-auxiliary layer and the hole transport layer, and the proper combination of the emission-auxiliary layer and the light emitting layer.
  • In order to fully exhibit the excellent characteristics of the organic electric element, materials forming the organic material layer in the element, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, an emission-auxiliary layer material, etc. should be prerequisite to support by a stable and efficient material, and in particular, it is strongly required to develop material of host of a light emitting layer, a hole transport layer and an emission-auxiliary layer.
    • Object, Technical Solution and Effects of the Invention
  • The present invention is to provide a compound lowering a driving voltage, improving luminous efficiency, color purity, stability and lifetime of the element, an organic electric element comprising the same, and an electronic device thereof.
  • In an aspect of the present invention, the present invention provides the compound represented by the following formula 1.
  • Figure US20220278285A1-20220901-C00001
  • In another aspect of the present invention, the present invention provides the compound represented by the following Formula A.
  • Figure US20220278285A1-20220901-C00002
  • In another aspect of the present invention, the present invention provides an organic electric element using the compound represented by formula 1 or A above and an electronic device thereof.
  • By using the compound according to embodiments of the present invention, a driving voltage can be lowered and the luminous efficiency, color purity, stability and lifetime of the element can be largely improved.
    • BRIEF DESCRIPTION OF THE DRAWINGS
  • The FIGURE illustrates an example of an organic electroluminescent element according to the present invention: 100 is organic electric element, 110 is substrate, 120 is first electrode, 130 is hole injection layer, 140 is hole transport layer, 141 is buffer layer, 150 is light emitting layer, 151 is emission-auxiliary layer, 160 is electron transport layer, 170 is electron injection layer, and 180 is second electrode.
    •  DETAILED DESCRIPTION
  • Unless otherwise stated, the term “aryl group” or “arylene group” as used herein has, but not limited to, 6 to 60 carbon atoms. The aryl group or arylene group in the present invention may comprise a monocyclic ring, ring assemblies, a fused polycyclic system, spiro compounds and the like.
  • The term “heterocyclic group” as used herein means a non-aromatic ring as well as an aromatic ring like “heteroaryl group” or “heteroarylene group”, and unless otherwise stated, it means a ring comprising one or more heteroatoms and having 2 to 60 carbon atoms, but not limited thereto. Unless otherwise stated, the term “hetero atom” as used herein represents N, O, S, P or Si, and the heterocyclic group means a monocyclic form, ring assemblies, a fused polycyclic system or a spiro compound comprising heteroatom(s).
  • The term “heterocyclic group” as used herein means a ring comprising a heteroatom like N, O, S, P, Si or the like instead of carbon consisting of a ring, it comprises a non-aromatic ring as well as an aromatic ring like “heteroaryl group” or “heteroarylene group” and the compound comprising the heteroatom group like SO2, P═O or the like instead of carbon consisting of a ring such as the following compound.
  • Figure US20220278285A1-20220901-C00003
  • Unless otherwise stated, the term “fluorenyl group” or “fluorenylene group” as used herein means univalent or bivalent functional group in which R, R′ and R″ are all hydrogen in the following structure, “substituted fluorenyl group” or “substituted fluorenylene group” means that at least any one of R, R′ and R″ is a substituent other than hydrogen, and it comprises spiro compound formed by linking R and R′ together with the carbon bonded to them.
  • Figure US20220278285A1-20220901-C00004
  • Unless otherwise stated, the term “spiro compound” as used herein has, a spiro union which means union having one atom as the only common member of two rings. The common atom is designated as ‘spiro atom’. The compounds are defined as ‘monospiro-’, ‘dispiro-’ or ‘trispiro-’ depending on the number of spiro atoms in one compound.
  • In the present description, a ‘group name’ corresponding to an aryl group, an arylene group, a heterocyclic group, and the like exemplified for each symbol and its substituent may be written in the name of functional group reflecting the valence, and may also be described under the name of a parent compound. For example, in the case of phenanthrene which is a kind of aryl group, it may be described by distinguishing valence such as ‘phenanthryl (group)’ when it is ‘monovalent group’, and as ‘phenanthrylene (group)’ when it is ‘divalent group’, and it may also be described as apparent compound name, ‘phenanthrene’, regardless of its valence. Similarly, in the case of pyrimidine, it may be described as ‘pyrimidine’ regardless of its valence, and it may also be described as the name of corresponding functional group such as pyrimidinyl (group) when it is ‘monovalent group’, and as ‘pyrimidylene (group)’ when it is ‘divalent group’.
  • Otherwise specified, the formulas used in the present invention are as defined in the index definition of the substituent of the following formula:
  • Figure US20220278285A1-20220901-C00005
  • Wherein, the substituent R1 is absent when a is an integer of zero, the sole R1 is bonded to any one of the carbon atoms constituting the benzene ring when a is an integer of 1, when a is an integer of 2 or 3, the substituent R1s may be bonded as follows and the substituents R1s may be the same or different each other, and the substituent R1s may be bonded to the carbon of the benzene ring in a similar manner when a is an integer of 4 to 6. Herein, the indication of the hydrogen bonded to the carbon which forms the benzene ring is omitted.
  • Figure US20220278285A1-20220901-C00006
  • Hereinafter, referring to the FIGURE, a lamination structure of an organic electric element including the compound of the present invention will be described.
  • The FIGURE illustrates an organic electric element according to an embodiment of the present invention.
  • Referring to the FIGURE, an organic electric element 100 according to an embodiment of the present invention includes a first electrode 120 formed on a substrate 110, a second electrode 180, and an organic material layer formed between the first electrode 120 and the second electrode 180 and comprising the compound of the present invention. Here, the first electrode 120 may be an anode (positive electrode), and the second electrode 180 may be a cathode (negative electrode). In the case of an inverted organic electric element, the first electrode may be a cathode, and the second electrode may be an anode.
  • The organic material layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 formed in sequence on the first electrode 120. Here, at least one layer of the organic material layer may be omitted, or the organic material layer may further include a hole blocking layer, an electron blocking layer, an emission-auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, etc., and the electron transport layer 160 or the like may serve as the hole blocking layer.
  • In addition, although not shown, the organic electric element according to an embodiment of the present invention may further include at least a protective layer or a layer for improving luminous efficiency. The layer for improving luminous efficiency may be formed on a surface that does not face the organic material layer of both surfaces of the first electrode or the second electrode.
  • The inventive compound employed in the organic material layer may be used as a material of a hole injection layer 130, a hole transport layer 140, an emission-auxiliary layer 151, an electron transport auxiliary layer, an electron transport layer 160, an electron injection layer 170 and the like, as a host or a dopant material of a light emitting layer 150, or as a material of a layer for improving luminous efficiency. For example, the compound according to Formula 1 of the present invention may be used as material of the light emitting layer 150, preferably, as host material of the light emitting layer 150, a mixture of the compound according to Formula 1 of the present invention and the compound according to Formula 12 of the present invention may be used as host material, and the compound according to Formula 20 of the present invention may be used as material of a hole transport layer or an emission-auxiliary layer. Preferably, the compound represented by Formula 21 or 22 of the present invention may be used as material of a hole transport layer, and the compound represented by Formula 23 or 24 of the present invention may be used as material of an emission-auxiliary layer. Also, the compound represented by Formula A of the present invention may be used as material of an emission-auxiliary layer, specially, a green emission-auxiliary layer.
  • Even if the core is the same core, the band gap, the electrical characteristics, the interface characteristics, and the like may be different depending on which substituent is bonded at which position. Therefore, it is necessary to study the selection of the core and the combination of the core and the sub-substituent bonded to the core. Specially, long life span and high efficiency can be simultaneously achieved when the optimal combination of energy levels and T1 values, inherent material properties (mobility, interfacial properties, etc.), and the like among the respective layers of an organic material layer is achieved.
  • Therefore, according to the present invention, energy level and T1 value between the respective layers of the organic material layer, inherent material properties (mobility, interfacial properties, etc.) and the like can be optimized by using as a host material of a light emitting layer a single compound represented by the Formula 1 or a mixture of the compound represented by the Formula 1 and the compound represented by the Formula 12, by using these compounds as a light-emitting layer material and simultaneously using the compound according to the formula 20 as a hole transport layer or an emission-auxiliary layer, and thus it is possible to simultaneously improve the life span and efficiency of the organic electric element.
  • The organic electric element according to an embodiment of the present invention may be manufactured using various deposition methods. The organic electric element according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) method or CVD (chemical vapor deposition) method. For example, the organic electric element may be manufactured by depositing a metal, a conductive metal oxide, or a mixture thereof on the substrate to form the anode 120, forming the organic material layer including the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the electron transport layer 160, and the electron injection layer 170 thereon, and then depositing a material, which can be used as the cathode 180, thereon. Also, an emitting auxiliary layer 151 may be formed between a hole transport layer 140 and a light emitting layer 150, and an electron transport auxiliary layer may be formed between a light emitting layer 150 and an electron transport layer 160.
  • Also, the organic material layer may be manufactured in such a manner that a smaller number of layers are formed using various polymer materials by a soluble process or solvent process, for example, spin coating, nozzle printing, inkjet printing, slot coating, dip coating, roll-to-roll, doctor blading, screen printing, or thermal transfer, instead of deposition. Since the organic material layer according to the present invention may be formed in various ways, the scope of protection of the present invention is not limited by a method of forming the organic material layer.
  • The organic electric element according to an embodiment of the present invention may be of a top emission type, a bottom emission type, or a dual emission type depending on the material used.
  • Also, the organic electric element according to an embodiment of the present invention may be any one of an organic light emitting diode, an organic solar cell, an organic photo conductor, an organic transistor, and an element for monochromatic or white illumination.
  • Another embodiment of the present invention provides an electronic device including a display device which includes the above described organic electric element, and a control unit for controlling the display device. Here, the electronic device may be a wired/wireless communication terminal which is currently used or will be used in the future, and covers all kinds of electronic devices including a mobile communication terminal such as a cellular phone, a personal digital assistant (PDA), an electronic dictionary, a point-to-multipoint (PMP), a remote controller, a navigation unit, a game player, various kinds of TVs, and various kinds of computers.
  • Hereinafter, the compound according to an aspect of the present invention will be described.
  • The compound according to an aspect of the present invention is represented by formula 1 below.
  • Figure US20220278285A1-20220901-C00007
  • In the formula 1, each of symbols may be defined as follows.
  • X1 and X2 are each independently O or S, provided that X1 and X2 are different from each other. That is, one of X1 and X2 is O and the other is S.
  • Ar1 to Ar3 are each independently selected from the group consisting of a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C1-C50 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxy group and -L′-N(Ra)(Rb).
  • When Ar1 to Ar3 are each an aryl group, Ar1 to Ar3 may be preferably a C6-C30 or a C6-C20 aryl group, more preferably a C6-C18 aryl group, for example, phenyl, biphenyl, naphthyl, phenanthryl, terphenyl or the like. When Ar1 to Ar3 are each a heterocyclic group, Ar1 to Ar3 may be preferably a C2-C30 or a C2-C20 heterocyclic group, more preferably a C2-C18 heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimidido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine and the like. When Ar1 to Ar3 are each a fluorenyl group, Ar1 to Ar3 may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene or the like.
  • When Ar2 and Ar3 are each an aryl group, Ar2 and Ar3 may be preferably a C6-C50 or a C6-C22 aryl group, more preferably a C6-C18 aryl group, for example, phenyl, biphenyl, naphthyl, phenanthryl, terphenyl or the like.
  • When Ar1 to Ar3 are each a heterocyclic group, Ar1 to Ar3 may be preferably a C2-C30 or a C2-C20 heterocyclic group, more preferably a C2-C18 heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimidido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine and the like. When Ar1 to Ar3 are each a fluorenyl group, Ar2 and Ar3 may be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene or the like.
  • R1 to R4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C50 aromatic ring, a C1-C50 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxy group and -L′-N(Ra)(Rb), and adjacent groups may be optionally linked to each other to form a C6-C60 aromatic ring, a C2-C60 heterocyclic group, a C3-C60 aliphatic ring, or a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring. Here, “adjacent groups are linked to each other” means that adjacent R1s, adjacent R2s, adjacent R3s, or adjacent R4s are respectively are linked to each other.
  • a to d are each an integer of 0 to 3, where each of these is an integer of 2 or more, each of R1s, each of R2s, each of R3s or each of R4s is the same or different from each other.
  • When R1 to R4 are each an aryl group, R1 to R4 may be preferably a C6-C30 or a C6-C20 aryl group, more preferably a C6-C18 aryl group, for example, phenyl, biphenyl, naphthyl, terphenyl or the like. When R1 to R4 are each a heterocyclic group, R1 to R4 may be preferably a C2-C30 or a C2-C20 heterocyclic group, more preferably a C2-C8 heterocyclic group, for example, triazine, pyrimidine, pyridine, quinazoline or the like.
  • The ring formed by linking between adjacent R1s, between adjacent R2s, between adjacent R3, or between adjacent R4 may be preferably a C6-C20 aromatic ring group, or a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, more preferably, a C6-C10 aromatic ring group, or a C2-C10 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, for example, benzene ring, naphthalene, phenanthrene, thiophene, benzothiophene, pyridine and the like. Therefore, when adjacent R1s to adjacent R4s are connected to each other to form a ring, an aromatic ring or a heterocycle comprising a benzene ring may be formed together with the benzene ring to which they are attached, preferably a C6-C14 aromatic ring or a C2-C14 heterocycle may be formed.
  • L′ is selected from the group consisting of a single bond, a C6-C60 arylene group, a fluorenylene group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring.
  • When L′ is an arylene group, L′ may be preferably a C6-C30 or C6-C20 arylene group, more preferably a C6-C18 arylene group, for example, phenylene, biphenyl, naphthalene, terphenyl or the like.
  • Ra and Rb are each independently selected from the group consisting of hydrogen, a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring.
  • When Ra and Rb are each an aryl group, Ra and Rb may be preferably a C6-C30 or C6-C20 aryl group, more preferably a C6-C18 aryl group, for example, phenyl, biphenyl, naphthyl, terphenyl or the like.
  • Ar1 to Ar3, R1 to R4, L′, Ra, Rb, and the ring formed by bonding between neighboring R1s to neighboring R4s may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20cycloalkyl group, a fused ring group formed by a C3-C50 aliphatic ring with a C6-C50 aromatic ring, a C7-C20 arylalkyl group, and a C8-C20 arylalkenyl group.
  • That is, where Ar1 to Ar3, R1 to R4, L′, Ra, Rb, and a ring formed by bonding between neighboring R1s to neighboring R4s are each an aryl group, an arylene group, an aromatic hydrocarbon, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring (group), a fused ring (group), an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group and the like, each of these may be further substituted with one or more substituents selected from the group consisting of substituents such as deuterium, halogen and the like.
  • For example, where Ar1 to Ar3, R1 to R4, L′, Ra, Rb, and a ring formed by bonding between neighboring R1s to neighboring R4s are further substituted with an aryl group, the aryl group is preferably a C6-C20 aryl group, more preferably, a C6-C18 aryl group, for example, phenyl, naphthyl, biphenyl, terphenyl, and the like.
  • In addition, where Ar1 to Ar3, R1 to R4, L′, Ra, Rb, and a ring formed by bonding between neighboring R1s to neighboring R4s are further substituted with a heterocyclic group, the heterocyclic group is preferably a C2-C20 heterocyclic group, more preferably, a C2-C12 heterocyclic group, for example, pyrazine, pyrimidine, pyridine, quinazoline, isoindole, carbazole, dibenzothiophene, and the like.
  • In addition, where Ar1 to Ar3, R1 to R4, L′, Ra, Rb, and a ring formed by bonding between neighboring R1s to R4s are further substituted with an alkyl group, the alkyl group is preferably a C1-C10 alkyl group, more preferably, a C1-C4 alkyl group, for example, methyl, t-butyl and the like.
  • In addition, Ar1 to Ar3, R1 to R4, L′, Ra, Rb, and a ring formed by bonding between neighboring R1s to R4s may be further substituted with the substituents such as F, CN, ethen and the like.
  • Formula 1 may be represented by one of the following Formula 2 to Formula 11.
  • Figure US20220278285A1-20220901-C00008
    Figure US20220278285A1-20220901-C00009
  • In Formulas 2 to 11, each symbol is as defined for Formula 1. For example, X1, X2, Ar1 to Ar3, R1 to R4, a, b, c and d are the same as defined for Formula 1.
  • Preferably, in Formulas 1 to 11, at least one of Ar1 to Ar3 may be a substituted or unsubstituted C6-C24 aryl group, more preferably, Ar1 to Ar3 may be all a substituted or unsubstituted C6-C12 aryl group, and Ar2 and Ar3 may be different from each other.
  • Specifically, the compound represented by formula 1 may be one of the following compounds, but it is not limited thereto.
  • Figure US20220278285A1-20220901-C00010
    Figure US20220278285A1-20220901-C00011
    Figure US20220278285A1-20220901-C00012
    Figure US20220278285A1-20220901-C00013
    Figure US20220278285A1-20220901-C00014
    Figure US20220278285A1-20220901-C00015
    Figure US20220278285A1-20220901-C00016
    Figure US20220278285A1-20220901-C00017
    Figure US20220278285A1-20220901-C00018
    Figure US20220278285A1-20220901-C00019
    Figure US20220278285A1-20220901-C00020
    Figure US20220278285A1-20220901-C00021
    Figure US20220278285A1-20220901-C00022
    Figure US20220278285A1-20220901-C00023
    Figure US20220278285A1-20220901-C00024
    Figure US20220278285A1-20220901-C00025
    Figure US20220278285A1-20220901-C00026
  • Figure US20220278285A1-20220901-C00027
    Figure US20220278285A1-20220901-C00028
    Figure US20220278285A1-20220901-C00029
    Figure US20220278285A1-20220901-C00030
    Figure US20220278285A1-20220901-C00031
    Figure US20220278285A1-20220901-C00032
    Figure US20220278285A1-20220901-C00033
    Figure US20220278285A1-20220901-C00034
    Figure US20220278285A1-20220901-C00035
    Figure US20220278285A1-20220901-C00036
    Figure US20220278285A1-20220901-C00037
    Figure US20220278285A1-20220901-C00038
    Figure US20220278285A1-20220901-C00039
    Figure US20220278285A1-20220901-C00040
    Figure US20220278285A1-20220901-C00041
    Figure US20220278285A1-20220901-C00042
    Figure US20220278285A1-20220901-C00043
    Figure US20220278285A1-20220901-C00044
    Figure US20220278285A1-20220901-C00045
    Figure US20220278285A1-20220901-C00046
    Figure US20220278285A1-20220901-C00047
    Figure US20220278285A1-20220901-C00048
  • Figure US20220278285A1-20220901-C00049
    Figure US20220278285A1-20220901-C00050
    Figure US20220278285A1-20220901-C00051
    Figure US20220278285A1-20220901-C00052
    Figure US20220278285A1-20220901-C00053
    Figure US20220278285A1-20220901-C00054
    Figure US20220278285A1-20220901-C00055
    Figure US20220278285A1-20220901-C00056
    Figure US20220278285A1-20220901-C00057
    Figure US20220278285A1-20220901-C00058
    Figure US20220278285A1-20220901-C00059
    Figure US20220278285A1-20220901-C00060
    Figure US20220278285A1-20220901-C00061
    Figure US20220278285A1-20220901-C00062
    Figure US20220278285A1-20220901-C00063
    Figure US20220278285A1-20220901-C00064
    Figure US20220278285A1-20220901-C00065
  • In another aspect of the present invention, the present invention provides an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises compound represented by Formula 1. The organic material layer comprises at least one layer of a hole injection layer, a hole transport layer, an emission-auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, preferably, the compound represented by Formula 1 is comprised in the light emitting layer, more preferably, a single compound or compounds of two or more kinds represented by Formula 1 may be used as host material of the light emitting layer.
  • In one embodiment according to the present invention, the light emitting layer may further comprise the compound represented by the following Formula 12.
  • Figure US20220278285A1-20220901-C00066
  • In Formula 12, each of symbols may be defined as follows.
  • Z1 to Z4, Z13 to Z16 are independently C(R) or N, Z5 to Z12 are independently C, C(R) or N.
  • L2 is selected from the group consisting of a single bond, a C6-C60 arylene group, a fluorenylene group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring.
  • When L2 is an arylene group, L2 may be preferably a C0-C30 or C6-C20 arylene group, more preferably a C6-C18 arylene group, for example, phenylene, naphthalene, biphenyl, terphenyl or the like. When L2 is a heterocyclic group, L2 may be preferably a C2-C30 or C2-C20 heterocyclic group, more preferably a C2-C18 heterocyclic group, for example, carbazole, phenylcarbazole or the like.
  • W is N(Ar5), N, O, S, C(R′) or C(R′)(R″), and W is N or C(R′) when W is combined with L2.
  • Ar4 and Ar5 are each independently selected from the group consisting of a C6-Cao aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C50 aliphatic ring, a fused ring group formed by a C3-C50 aliphatic ring with a C6-C60 aromatic ring, a C1-C50 alkyl group, a C2-C20 alkenyl group, a C2-C2a alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxy group, -L′-N(Ra)(Rb) and a combination thereof. Here, the term “a combination thereof” means, for example, a combination of an aryl group and a heterocyclic group, a combination of an aryl group and an aliphatic ring, a combination of a heterocyclic group and an aliphatic ring group, and the like.
  • R, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C6-C50 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C1-C60 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxy group and -L′-N(Ra)(Rb), adjacent R groups may be optionally linked to each other to form a ring, and R′ and R″ may be optionally linked to each other to form a ring.
  • The ring formed by linking between adjacent R groups or between R′ and R″ may be a C6-C60 aromatic ring group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring, or a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, preferably, a C6-C20 aromatic ring group or a C2-C20 heterocyclic group, more preferably, a C6-C10 aromatic ring group or a C2-C10 heterocyclic group, for example, benzene, naphthalene, phenanthrene, thiophene, benzothiophene, pyridine and the like.
  • L′, Ra and Rb are the same as defined for Formula 1.
  • L2, Ar4, Ar5, R, R′, R″, the ring formed by linking between adjacent R groups, and the ring formed by linking between R′ and R″ may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C7-C20 arylalkyl group, and a C8-C20 arylalkenyl group.
  • Preferably, Formula 12 is represented by one of Formulas 13 to 17.
  • Figure US20220278285A1-20220901-C00067
  • In Formulas 13 to 17, Ar4, Ar5, Z1 to Z16, L2, R and R are the same as defined for Formula 12.
  • Preferably, in Formulas 13 to 17, at least one of Ar4 and Ar5 may be a substituted or unsubstituted C6-C30 aryl group, more preferably, both Ar4 and Ar5 are a C6-C30 aryl group.
  • Preferably, Formula 12 may be represented by Formula 18 or Formula 19.
  • Figure US20220278285A1-20220901-C00068
  • In Formulas 18 and 19, each of symbols may be defined as follows.
  • Ar4, Z1 to Z16, and L2 are the same as defined for Formula 12.
  • L1 is selected from the group consisting of a single bond, a C6-C60 arylene group, a fluorenylene group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring.
  • When L1 is an arylene group, L1 may be preferably a C6-C30 or C6-C20 arylene group, more preferably a C6-C12 arylene group, for example, phenylene, naphthalene, biphenyl or the like,
  • Y is O, S or N—Ar6.
  • Ra and Rb are each independently selected from the group consisting of deuterium, halogen, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C7-C20 arylalkyl group and a C8-C20 arylalkenyl group, and adjacent groups may be optionally linked to each other to form a C6-C60 aromatic ring, a C2-C60 heterocyclic group, a C3-C60 aliphatic ring, or a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring.
  • y is an integer of 0 to 3, and z is an integer of 0 to 4, where each of these is an integer of 2 or more, each of Ras, each of Rbs is the same or different from each other.
  • Ar6 is selected from the group consisting of a C6-C60 aryl group, a C6-C60 aryl group substituted with deuterium, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 cycloalkyl group, a fused ring group formed by a C3-C50 aliphatic ring with a C6-C60 aromatic ring, a C1-C60 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxy group, a C7-C20 arylalkyl group and a C8-C20 arylalkenyl group. Preferably, Ar6 is selected from the group consisting of a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C7-C20 arylalkyl group and a C8-C20 arylalkenyl group.
  • Specifically, the compound represented by formula 12 may be one of the following compounds, but it is not limited thereto.
  • Figure US20220278285A1-20220901-C00069
    Figure US20220278285A1-20220901-C00070
    Figure US20220278285A1-20220901-C00071
    Figure US20220278285A1-20220901-C00072
    Figure US20220278285A1-20220901-C00073
    Figure US20220278285A1-20220901-C00074
    Figure US20220278285A1-20220901-C00075
    Figure US20220278285A1-20220901-C00076
    Figure US20220278285A1-20220901-C00077
  • Figure US20220278285A1-20220901-C00078
    Figure US20220278285A1-20220901-C00079
    Figure US20220278285A1-20220901-C00080
    Figure US20220278285A1-20220901-C00081
    Figure US20220278285A1-20220901-C00082
    Figure US20220278285A1-20220901-C00083
    Figure US20220278285A1-20220901-C00084
    Figure US20220278285A1-20220901-C00085
    Figure US20220278285A1-20220901-C00086
    Figure US20220278285A1-20220901-C00087
    Figure US20220278285A1-20220901-C00088
    Figure US20220278285A1-20220901-C00089
    Figure US20220278285A1-20220901-C00090
  • Preferably, the organic material layer of an organic element according to the present invention comprises a light emitting layer, a hole transport layer formed between the first electrode and the light emitting layer, and an emission-auxiliary layer formed between the light emitting layer and the hole transport layer, the light emitting layer comprises the compound represented by Formula 1, and the hole transport layer or the emission-auxiliary layer comprises the compound represented by Formula 20.
  • Figure US20220278285A1-20220901-C00091
  • In Formula 20, each of symbols may be defined as follows.
  • Ar4 and Ar5 are each independently selected from the group consisting of a C6-C50 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C1-C50 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxy group and -L′-N(Ra)(Rb), and Ar4 and Ar5 may be combined with each other to form a ring.
  • Ar6 is selected from the group consisting of a C6-C60 aryl group, a fluorenyl group, and a C2-C50 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; or Ar6 is selected from the group consisting of the following Formulas 1-a to 1-c.
  • Figure US20220278285A1-20220901-C00092
  • In Formula 1-a to 1-c, each of symbols may be defined as follows.
  • Ar9 to Ar11 are each independently selected from the group consisting of a C6-C50 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C1-C50 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxy group and -L′-N(Ra)(Rb).
  • L5 is selected from the group consisting of a C6-C60 arylene group, a fluorenylene group, and a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring.
  • L6 is selected from the group consisting of a single bond, a C6-C60 arylene group, a fluorenylene group, and a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C50 aromatic ring.
  • R6 to R9 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C50 aromatic ring, a C1-C50 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxy group and -L′-N(Ra)(Rb).
  • h, i and g are each an integer of 0 to 4, j is an integer of 0 to 3, where each of these is an integer of 2 or more, a plurality of R6s, a plurality of R7s, a plurality of R8s, a plurality of R9s are the same as or different from each other. In addition, when h, i, j and g are each an integer of 2 or more, adjacent R6 groups, adjacent R7 groups, adjacent R8 groups, or adjacent R9 groups may be linked to each other to form a ring. Here, the ring formed by linking between adjacent groups may be a C6-C60 aromatic ring group, a C2-C50 heterocyclic group, a C3-C50 aliphatic ring, or a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring.
  • L′, Ra and Rb are the same as defined for Formula 1.
  • Ar4 to Ar6, Ar9 to Ar11, R6 to R9, L5, L6, and the ring formed by bonding between neighboring groups may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C7-C20 arylalkyl group, a C8-C20 arylalkenyl group and a combination thereof.
  • Preferably, the light emitting layer may further comprise the compound represented by Formula 12.
  • Preferably, the hole transport layer comprises the compound represented by the following Formula 21 or Formula 22 and the emission-auxiliary layer comprises the compound represented by the following Formula 23 or Formula 24.
  • Figure US20220278285A1-20220901-C00093
  • In Formulas 21 to 24, Ar4, Ar5, Ar9 to Ar11, h, i, g, j, L5, L6, R6 to R9 are the same as defined above, Ar7 is selected from the group consisting of a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, and a C3-C60 aliphatic ring. Preferably, in Formula 24, at least one of Ar4, Ar5, Ar10 and Ar11 may be represented by Formula 24-1.
  • Figure US20220278285A1-20220901-C00094
  • In Formula 24-1, each of symbols may be defined as follows.
  • Ra′, Rb′ and Rc′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C3-C20 cycloalkyl group, and a fused ring group formed by a C3-C50 aliphatic ring with a C6-C60 aromatic ring, and adjacent groups may be optionally linked to each other to form a ring. When adjacent Ra′ groups, adjacent Rb′ groups, or adjacent Rc′ groups are linked to each other to form a ring, the ring may be a C6-C60 aromatic ring group, a C2-C60 heterocyclic group, a C3-C60 aliphatic ring, or a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring.
  • I′, m′ and n′ are each an integer of 0 to 4, where each of these is an integer of 2 or more, a plural of Ra′s, a plural of Rb′s or a plural of Rc′s are each the same or different from each other.
  • Ar1′ is selected from the group consisting of a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C3-C20 cycloalkyl group, and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring.
  • Ra′, Rb′, Rc′, Ar1′ and the ring formed by bonding between neighboring may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C7-C20 arylalkyl group, a C8-C20 arylalkenyl group and a combination thereof.
  • In addition, preferably, in Formula 24, Ar1′ and L5 are each independently a C6-C60 arylene group, for example, phenyl, biphenyl, o-terphenyl, m-terphenyl, p-terphenyl or naphthalene.
  • Preferably, Formula 24 may be represented by the following Formula A.
  • <Formula A>
  • Figure US20220278285A1-20220901-C00095
  • In Formula A, Ra′, Rb′, Rc′, Ar1′, l′, m′ and n′ are the same as defined for Formula 24-1, Ar2′ is the same as defined for Ar11 in Formula 24, Ar3′ is the same as defined for Ar4 in Formula 24, Ar4, is the same as defined for Ar5 in Formula 24, and a′ is an integer of 1 to 3. That is, in Formula A, each of symbols may be defined as follows.
  • Ra′, Rb′ and Rc′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C3-C20 cycloalkyl group, and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C50 aromatic ring, and adjacent groups may be optionally linked to each other to form a ring. When adjacent Ra′ groups, adjacent Rb′ groups, or adjacent Rc′ groups are linked to each other to form a ring, the ring may be a C6-C60 aromatic ring group, a C2-C50 heterocyclic group, a C3-C50 aliphatic ring, or a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring.
  • l′, m′ and n′ are each an integer of 0 to 4, where each of these is an integer of 2 or more, a plural of Ra′s, a plural of Rb′s or a plural of Rc′s are each the same or different from each other.
  • Ar1′ is selected from the group consisting of a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C3-C20 cycloalkyl group, and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring.
  • Where Ar1′ is an aryl group, Ar1′ may be preferably a C6-C18 aryl group, more preferably a C6-C12 aryl group, for example, phenyl, biphenyl, terphenyl, naphthyl or the like.
  • Ar2′, Ar3′ and Ar4′ are each independently selected from the group consisting of a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C1-C60 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxy group and -L′-N(Ra)(Rb), Ar4 and Ar5 may be linked to each other to form a ring.
  • Where Ar2′ is an aryl group, Ar2′ may be preferably a C6-C30 aryl group, more preferably a C6-C18 aryl group, for example, phenyl, naphthyl, biphenyl, terphenyl or the like. Where Ar2′ is a heterocyclic group, Ar2′ may be preferably a C2-C30 heterocyclic group, more preferably a C2-C16 heterocyclic group, for example, dibenzofuran, dibenzothiophene and the like. Where Ar2′ is a fluorenyl group, Ar2′ may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9′-spirobifluorene and the like.
  • Where Ar3′ and Ar4′ are each an aryl group, Ar3′ and Ar4′ may be preferably a C6-C30 aryl group, more preferably a C6-C18 aryl group, for example, phenyl, biphenyl, terphenyl, naphthyl, triphenylene, phenanthrene or the like. Where Ar3′ and Ar4′ are each a heterocyclic group, Ar3′ and Ar4′ may be preferably a C2-C30 heterocyclic group, more preferably a C2-C12 heterocyclic group, for example, dibenzofuran, dibenzothiophene and the like. Where Ar3′ and Ar4′ are each a fluorenyl group, Ar3′ and Ar4′ may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9′-spirobifluorene and the like.
  • L′ is selected from the group consisting of a single bond, a C6-C60 arylene group, a fluorenylene group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring,
  • Ra and Rb are each independently selected from the group consisting of hydrogen, a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring.
  • Ra′, Rb′, Rc′, Ra, Rb, Ar1′ to Ar4′, L′ and a ring formed by bonding between neighboring groups may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C7-C20 arylalkyl group, a C8-C20 arylalkenyl group and a combination thereof.
  • Formula A may be represented by one of Formula B to Formula D.
  • Figure US20220278285A1-20220901-C00096
  • In Formulas B to D, Ra′, Rb′, Rc′, l′, m′, n′, Ar1′ to Ar4′ are the same as defined for Formula A.
  • In addition, Formula A may be represented by one of Formula E to Formula G.
  • Figure US20220278285A1-20220901-C00097
  • In Formulas E to G, Ra′, Rb′, Rc′, l′, m′, n′, Ar1′ to Ar4′ are the same as defined for Formula A.
  • In addition, Formula A may be represented by one of Formula H to Formula K.
  • Figure US20220278285A1-20220901-C00098
  • In Formulas H to K, Ra′, Rb′, Rc′, l′, m′, n′, Ar1′ to Ar3′ are the same as defined for Formula A.
  • X is independently O, S or C(R′)(R″),
  • Rd′, Re′, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C3-C20 cycloalkyl group, and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, and adjacent groups may be optionally linked to each other to form a ring. Where adjacent Rd′ groups or adjacent Re′ groups are linked to each other to form a ring, the ring may be a C6-C60 aromatic ring group, a C2-C60 heterocyclic group, a C3-C60 aliphatic ring, or a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, and when R′ group and R″ group are linked to each other to form a ring, a spiro compound may be formed together with C to which they are attached.
  • o′ is independently an integer of 0 to 3, p′ is independently an integer of 0 to 4, where o′ is an integer of 2 or more, a plural of Rd′s are each the same or different from each other, where p′ is an integer of 2 or more, a plural of Re′s are each the same or different from each other.
  • Rd′, Re′, R′, R″ and the ring formed by bonding between neighboring groups may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C7-C20 arylalkyl group, a C8-C20 arylalkenyl group and a combination thereof.
  • Formula A may be represented by one of Formula L to Formula O.
  • Figure US20220278285A1-20220901-C00099
    Figure US20220278285A1-20220901-C00100
  • In Formulas H to K, Ra′, Rb′, Rc′, l′, m′, n′, Ar3′ and Ar4′ are the same as defined for Formula A.
  • Re′, Rf′, Rg′, Rh′ and Rl′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C3-C20 cycloalkyl group, and a fused ring group formed by a C3-C50 aliphatic ring with a C6-C60 aromatic ring, and adjacent groups may be optionally linked to each other to form a ring. Where adjacent Re′ groups, adjacent Rf′ groups, adjacent Rg′ groups, adjacent Rh′ groups, or adjacent Rl′ groups are linked to each other to form a ring, the ring may be a C6-C60 aromatic ring group, a C2-C60 heterocyclic group, a C3-C50 aliphatic ring, or a fused ring group formed by a C3-C50 aliphatic ring with a C6-C60 aromatic ring.
  • p′, r′ and t′ are each independently an integer of 0 to 3, q′ and s′ are each independently an integer of 0 to 4, where each of these is an integer of 2 or more, each of Re′s, each of Rf′s, each of Rg′s, each of Rh′s, and each of Rl′s is each the same or different from each other.
  • b′ is an integer of 0 to 3.
  • Re′, Rf′, Rg′, Rh′, Rl′ and the ring formed by bonding between neighboring groups may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C7-C20 arylalkyl group, a C8-C20 arylalkenyl group and a combination thereof.
  • Specifically, the compound represented by formula 20 may be one of the following compounds, but it is not limited thereto.
  • Figure US20220278285A1-20220901-C00101
    Figure US20220278285A1-20220901-C00102
    Figure US20220278285A1-20220901-C00103
    Figure US20220278285A1-20220901-C00104
    Figure US20220278285A1-20220901-C00105
    Figure US20220278285A1-20220901-C00106
    Figure US20220278285A1-20220901-C00107
    Figure US20220278285A1-20220901-C00108
    Figure US20220278285A1-20220901-C00109
    Figure US20220278285A1-20220901-C00110
    Figure US20220278285A1-20220901-C00111
    Figure US20220278285A1-20220901-C00112
    Figure US20220278285A1-20220901-C00113
    Figure US20220278285A1-20220901-C00114
  • Figure US20220278285A1-20220901-C00115
    Figure US20220278285A1-20220901-C00116
    Figure US20220278285A1-20220901-C00117
    Figure US20220278285A1-20220901-C00118
    Figure US20220278285A1-20220901-C00119
    Figure US20220278285A1-20220901-C00120
    Figure US20220278285A1-20220901-C00121
    Figure US20220278285A1-20220901-C00122
    Figure US20220278285A1-20220901-C00123
    Figure US20220278285A1-20220901-C00124
    Figure US20220278285A1-20220901-C00125
    Figure US20220278285A1-20220901-C00126
    Figure US20220278285A1-20220901-C00127
    Figure US20220278285A1-20220901-C00128
    Figure US20220278285A1-20220901-C00129
    Figure US20220278285A1-20220901-C00130
  • Specifically, the compound represented by formula A may be one of the following compounds, but it is not limited thereto.
  • Figure US20220278285A1-20220901-C00131
    Figure US20220278285A1-20220901-C00132
    Figure US20220278285A1-20220901-C00133
    Figure US20220278285A1-20220901-C00134
    Figure US20220278285A1-20220901-C00135
    Figure US20220278285A1-20220901-C00136
    Figure US20220278285A1-20220901-C00137
    Figure US20220278285A1-20220901-C00138
    Figure US20220278285A1-20220901-C00139
    Figure US20220278285A1-20220901-C00140
    Figure US20220278285A1-20220901-C00141
    Figure US20220278285A1-20220901-C00142
    Figure US20220278285A1-20220901-C00143
    Figure US20220278285A1-20220901-C00144
    Figure US20220278285A1-20220901-C00145
    Figure US20220278285A1-20220901-C00146
    Figure US20220278285A1-20220901-C00147
    Figure US20220278285A1-20220901-C00148
    Figure US20220278285A1-20220901-C00149
    Figure US20220278285A1-20220901-C00150
    Figure US20220278285A1-20220901-C00151
    Figure US20220278285A1-20220901-C00152
  • Figure US20220278285A1-20220901-C00153
    Figure US20220278285A1-20220901-C00154
    Figure US20220278285A1-20220901-C00155
    Figure US20220278285A1-20220901-C00156
    Figure US20220278285A1-20220901-C00157
    Figure US20220278285A1-20220901-C00158
    Figure US20220278285A1-20220901-C00159
    Figure US20220278285A1-20220901-C00160
    Figure US20220278285A1-20220901-C00161
    Figure US20220278285A1-20220901-C00162
    Figure US20220278285A1-20220901-C00163
    Figure US20220278285A1-20220901-C00164
  • Figure US20220278285A1-20220901-C00165
    Figure US20220278285A1-20220901-C00166
    Figure US20220278285A1-20220901-C00167
    Figure US20220278285A1-20220901-C00168
    Figure US20220278285A1-20220901-C00169
    Figure US20220278285A1-20220901-C00170
    Figure US20220278285A1-20220901-C00171
    Figure US20220278285A1-20220901-C00172
    Figure US20220278285A1-20220901-C00173
    Figure US20220278285A1-20220901-C00174
    Figure US20220278285A1-20220901-C00175
    Figure US20220278285A1-20220901-C00176
    Figure US20220278285A1-20220901-C00177
    Figure US20220278285A1-20220901-C00178
    Figure US20220278285A1-20220901-C00179
    Figure US20220278285A1-20220901-C00180
    Figure US20220278285A1-20220901-C00181
    Figure US20220278285A1-20220901-C00182
    Figure US20220278285A1-20220901-C00183
    Figure US20220278285A1-20220901-C00184
    Figure US20220278285A1-20220901-C00185
    Figure US20220278285A1-20220901-C00186
  • In another aspect of the present invention, the present invention provides an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a single compound or compounds of two or more kinds represented by Formula 1.
  • In another aspect of the present invention, the present invention provides an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a single compound or compounds of two or more kinds represented by Formula A.
  • The organic material layer comprises at least one layer of a hole injection layer, a hole transport layer, an emission-auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, and preferably, the compound represented by Formula 1 may be comprised in a light emitting layer and the compound represented by Formula A may be comprised in an emission-auxiliary layer, in particular, a green emission-auxiliary layer.
  • In another aspect of the present invention, the present invention provides an electronic device comprising a display device comprising the organic electric element, and a control unit for driving the display device, wherein the organic electric element comprises the compound represented by Formula 1 or A.
  • Hereinafter, synthesis examples of the compounds represented by Formulas 1, 12, 20 and A, respectively, and preparation methods of an organic electric element according to one embodiment of the present invention will be described in detail by way of examples. However, the present invention is not limited to the following examples.
    • Synthesis Example Synthesis Example 1
  • As shown in Reaction Scheme 1 below, the compound represented by Formula according to the present invention can be synthesized by reacting Sub 1 with Sub 2.
  • Figure US20220278285A1-20220901-C00187
    • 1. Synthesis Example of Sub 1
  • Sub 1 of the Reaction Scheme 1 can be synthesized according to the reaction route of the following Reaction Scheme 2, but there is no limitation thereto.
  • Figure US20220278285A1-20220901-C00188
  • Synthesis of Sub 1-2
  • Figure US20220278285A1-20220901-C00189
  • After 2,4-dichloro-6-phenyl-1,3,5-triazine (25 g, 110.59 mmol) and (6-([1,1′-biphenyl]-3-yl)dibenzo[b,d]thiophen-4-yl)boronic acid (92.52 g, 243.30 mmol) were dissolved in THF (590 ml), Pd(PPh3)4 (5.11 g, 4.42 mmol), K2CO3 (45.85 g, 331.77 mmol) and water (295 ml) were added thereto and the mixture was stirred under reflux. When the reaction was completed, the reaction product was extracted with ether and water and the organic layer was concentrated. The concentrated organic layer was dried with MgSO4 and concentrated. Thereafter, the concentrate was applied to a silica gel column to obtain 46.54 g (yield: 80%) of the product.
  • Synthesis of Sub 1-12
  • Figure US20220278285A1-20220901-C00190
  • (6-([1,1′-biphenyl]-3-yl)benzo[b]naphtho[1,2-d]thiophen-8-yl)boronic acid (104.70 g, 243.30 mmol), Pd(PPh3)4 (0.04 eq.), K2CO3 (3 eq.), anhydrous THE and a small amount of water were added to 2,4-dichloro-6-phenyl-1,3,5-triazine (25 g, 110.59 mmol), and then 44.60 g (yield: 70%) of the product was obtained by the same method as in synthesis of Sub 1-2.
  • Synthesis of Sub 1-15
  • Figure US20220278285A1-20220901-C00191
  • (7-(2-(pyrazin-2-yl)phenyl)dibenzo[b,d]thiophen-4-yl)boronic acid (76.14 g, 199.19 mmol), Pd(PPh3)4 (0.04 eq.), K2CO3 (3 eq.), anhydrous THE and a small amount of water were added to 2,4-dichloro-6-(naphthalen-2-yl)-1,3,5-triazine (25 g, 90.54 mmol), and then 35.59 g (yield: 68%) of the product was obtained by the same method as in synthesis of Sub 1-2.
  • Synthesis of Sub 1-22
  • Figure US20220278285A1-20220901-C00192
  • (8-(2-(2H-isoindol-2-yl)phenyl)dibenzo[b,d]thiophen-4-yl)boronic acid (116.77 g, 278.47 mmol), Pd(PPh3)4 (0.04 eq.), K2CO3 (3 eq.), anhydrous THE and a small amount of water were added to 2,4-dichloro-6-(perfluorophenyl)-1,3,5-triazine (40 g, 126.58 mmol), and then 49.75 g (yield: 60%) of the product was obtained by the same method as in synthesis of Sub 1-2.
  • Synthesis of Sub 1-37
  • Figure US20220278285A1-20220901-C00193
  • (7-(9H-carbazol-9-yl)dibenzo[b,d]furan-4-yl)boronic acid (157.85 g, 418.47 mmol), Pd(PPh3)4 (0.04 eq.), K2CO3 (3 eq.), anhydrous THE and a small amount of water were added to 2,4-dichloro-6-phenyl-1,3,5-triazine (43 g, 190.21 mmol), and then 64.66 g (yield: 65%) of the product was obtained by the same method as in synthesis of Sub 1-2.
  • Synthesis of Sub 1-67
  • Figure US20220278285A1-20220901-C00194
  • (6-(phenyl-d5)dibenzo[b,d]thiophen-4-yl)boronic acid (135.41 g, 437.94 mmol), Pd(PPh3)4 (0.04 eq.), K2CO3 (3 eq.), anhydrous THE and a small amount of water were added to 2,4-dichloro-6-phenyl-1,3,5-triazine (45 g, 199.06 mmol), and then 68.83 g (yield: 76%) of the product was obtained by the same method as in synthesis of Sub 1-2.
  • Synthesis of Sub 1-70
  • Figure US20220278285A1-20220901-C00195
  • 5-([1,1′-biphenyl]-3-yl)benzo[b]naphtho[1,2-d]thiophen-10-yl)boronic acid (188.46 g, 437.94 mmol), Pd(PPh3)4 (0.04 eq.), K2CO3 (3 eq.), anhydrous THE and a small amount of water were added to 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (45 g, 199.06 mmol), and then 72.25 g (yield: 63%) of the product was obtained by the same method as in synthesis of Sub 1-2.
  • Synthesis of Sub 1-74
  • Figure US20220278285A1-20220901-C00196
  • (8-([1,1′-biphenyl]-3-yl)dibenzo[b,d]furan-3-yl)boronic acid (177.22 g, 486.60 mmol), Pd(PPh3)4 (0.04 eq.), K2CO3 (3 eq.), anhydrous THE and a small amount of water were added to 2,4-dichloro-6-phenyl-1,3,5-triazine (50 g, 221.18 mmol), and then 81.22 g (yield: 72%) of the product was obtained by the same method as in synthesis of Sub 1-2.
  • The compound belonging to Sub 1 may be, but not limited to, the following compounds, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub 1.
  • Figure US20220278285A1-20220901-C00197
    Figure US20220278285A1-20220901-C00198
    Figure US20220278285A1-20220901-C00199
    Figure US20220278285A1-20220901-C00200
    Figure US20220278285A1-20220901-C00201
    Figure US20220278285A1-20220901-C00202
    Figure US20220278285A1-20220901-C00203
    Figure US20220278285A1-20220901-C00204
    Figure US20220278285A1-20220901-C00205
    Figure US20220278285A1-20220901-C00206
    Figure US20220278285A1-20220901-C00207
    Figure US20220278285A1-20220901-C00208
    Figure US20220278285A1-20220901-C00209
    Figure US20220278285A1-20220901-C00210
    Figure US20220278285A1-20220901-C00211
    Figure US20220278285A1-20220901-C00212
    Figure US20220278285A1-20220901-C00213
    Figure US20220278285A1-20220901-C00214
    Figure US20220278285A1-20220901-C00215
    Figure US20220278285A1-20220901-C00216
    Figure US20220278285A1-20220901-C00217
    Figure US20220278285A1-20220901-C00218
  • TABLE 1
    Compound FD-MS Compound FD-MS
    Sub 1-1 m/z = 449.08 (C27H16ClN3S = 449.96) Sub 1-2 m/z = 525.11 (C33H20ClN3S = 526.05)
    Sub 1-4 m/z = 499.09 (C31H18ClN3S = 500.02) Sub 1-6 m/z = 575.12 (C37H22ClN3S = 576.11)
    Sub 1-7 m/z = 606.17 (C39H19D5ClN3S = 607.18) Sub 1-8 m/z = 544.09 (C32H18ClFN4S = 545.03)
    Sub 1-9 m/z = 505.14 (C31H24ClN3S = 506.06) Sub 1-10 m/z = 557.05 (C31H16ClN5S2 = 558.07)
    Sub 1-11 m/z = 599.12 (C39H22ClN3S = 600.14) Sub 1-12 m/z = 575.12 (C37H22ClN3S = 576.11)
    Sub 1-15 m/z = 577.11 (C35H20ClN5S = 578.09) Sub 1-16 m/z = 575.12 (C37H22ClN3S = 576.11)
    Sub 1-17 m/z = 601.11 (C37H20ClN5S = 602.11) Sub 1-20 m/z = 617.11 (C37H20ClN5OS = 618.11)
    Sub 1-21 m/z = 601.14 (C39H24ClN3S = 602.15) Sub 1-22 m/z = 654.07 (C35H16ClF5N4S = 655.04)
    Sub 1-25 m/z = 526.10 (C32H19ClN4S = 527.04) Sub 1-26 m/z = 666.16 (C43H27ClN4S = 667.23)
    Sub 1-27 m/z = 536.09 (C31H13D5ClN3S2 = 537.11) Sub 1-28 m/z = 499.09 (C31H18ClN3S = 500.02)
    Sub 1-31 m/z = 518.08 (C30H16ClFN4S = 518.99) Sub 1-32 m/z = 455.12 (C27H22ClN3S = 456.00)
    Sub 1-34 m/z = 509.13 (C33H20ClN3O = 509.99) Sub 1-35 m/z = 433.10 (C27H16ClN3O = 433.90)
    Sub 1-36 m/z = 635.18 (C43H26ClN3O = 636.15) Sub 1-37 m/z = 522.12 (C33H19ClN4O = 522.99)
    Sub 1-38 m/z = 603.13 (C37H22ClN5S = 604.13) Sub 1-41 m/z = 483.11 (C31H18ClN3O = 483.96)
    Sub 1-43 m/z = 561.14 (C35H20ClN5O = 562.03) Sub 1-44 m/z = 626.13 (C40H23ClN4S = 627.16)
    Sub 1-46 m/z = 615.12 (C39H22ClN3OS = 616.14) Sub 1-50 m/z = 611.15 (C39H22ClN5O = 612.09)
    Sub 1-52 m/z = 632.14 (C39H25ClN4OS = 633.17) Sub 1-54 m/z = 655.22 (C43H22D5ClN4O = 656.20)
    Sub 1-55 m/z = 527.10 (C31H18ClN5S = 528.03) Sub 1-56 m/z = 559.15 (C37H22ClN3O = 560.05)
    Sub 1-60 m/z = 576.12 (C36H21ClN4S = 577.10) Sub 1-61 m/z = 509.13 (C33H20ClN3O = 509.99)
    Sub 1-62 m/z = 605.13 (C38H24ClN3OS = 606.14) Sub 1-63 m/z = 599.14 (C39H22ClN3O2 = 600.07)
    Sub 1-65 m/z = 602.13 (C38H23ClN4S = 603.14) Sub 1-66 m/z = 680.15 (C42H25ClN6S = 681.21)
    Sub 1-67 m/z = 454.11 (C27H11D5ClN3S = 454.99) Sub 1-68 m/z = 525.11 (C33H20ClN3S = 526.05)
    Sub 1-69 m/z = 544.09 (C32H18ClFN4S = 545.03) Sub 1-70 m/z = 575.12 (C37H22ClN3S = 576.11)
    Sub 1-71 m/z = 449.08 (C27H16ClN3S = 449.96) Sub 1-71 m/z = 525.11 (C33H20ClN3S = 526.05)
    Sub 1-73 m/z = 449.08 (C27H16ClN3S = 449.96) Sub 1-74 m/z = 509.13 (C33H20ClN3O = 509.99)
    • 2. Synthesis Example of Sub 2
  • Sub 2 of the Reaction Scheme 1 can be synthesized according to the reaction route of the following Reaction Scheme 3, but there is no limitation thereto.
  • Figure US20220278285A1-20220901-C00219
  • Synthesis of Sub 2-3
  • Figure US20220278285A1-20220901-C00220
  • After 4-([1,1′-biphenyl]-3-yl)-6-bromodibenzo[b,d]furan (CAS Registry Number: 1010068-89-9) (50 g, 125.22 mmol) were dissolved in THF (522 ml), the temperature of the reactant was lowered to −78° C. Thereafter, n-BuLi (2.5M in hexane) (12.03 g, 187.83 mmol) was added slowly thereto and the mixture was stirred at 0° C. for 1 hour. Thereafter, the temperature of the reactant was lowered to −78° C., triisopropyl borate (28.26 g, 150.27 mmol) and water (261 ml) were added thereto and the mixture was stirred at room temperature for 12 hour. When reaction was completed, the product was extracted with ether and water. Then, the organic layer was dried with MgSO4 and concentrated. The concentrate was applied to silica gel column and recrystallized to obtain 36.49 g (yield: 80%) of the product.
  • Synthesis of Sub 2-7
  • Figure US20220278285A1-20220901-C00221
  • (1) Synthesis of Sub 2-1-1
  • After dibenzo[b,d]furan-4-ylboronic acid (50 g, 235.84 mmol) and 7-bromo-5-phenyl-5H-pyrimido[5,4-b]indole (91.74 g, 283.01 mmol) were dissolved in THF (865 mL), Pd(PPh3)4 (10.90 g, 9.43 mmol), K2CO3 (97.79 g, 707.51 mmol) and water (432 ml) were added thereto and the mixture was stirred under reflux. When reaction was completed, the product was extracted with ether and water. Then, the organic layer was concentrated and dried with MgSO4 and concentrated. Thereafter, concentrate was applied to silica gel column and recrystallized to obtain 53.37 g (yield: 55%) of the product.
  • (2) Synthesis of Sub 2-1-2
  • After 7-(dibenzo[b,d]furan-4-yl)-5-phenyl-5H-pyrimido[5,4-b]indole (53.37 g, 129.71 mmol) were dissolved in THF (476 mL), the temperature of the reactant was lowered to −75° C. Thereafter, n-BuLi(2.5M in hexane) (9.97 g, 155.65 mmol) was added slowly thereto and the solution was stirred at room temperature for 1 hour. Thereafter, the temperature of the reactant was lowered to −75° C., l2 (49.38 g, 194.56 mmol) and water (238 mL) were added thereto and the mixture was stirred at room temperature for 17 hour. Thereafter, aqueous solution of sodium thiosulfate was added thereto and the mixture was stirred for 1 hour. When reaction was completed, the product was extracted with ether and water. Then, the organic layer was dried with MgSO4 and concentrated. The concentrate was applied to silica gel column and recrystallized to 41.82 g (yield: 60%) of the product.
  • (3) Synthesis of Sub 2-7
  • THF (324 mL), n-BuLi(2.5M in hexane) (7.48 g, 116.74 mmol), triisopropyl borate (17.56 g, 93.39 mmol) and water (162 mL) were added to 6-(5-phenyl-5H-pyrimido[5,4-b]indol-7-yl)dibenzo[b,d]furan-4-yl)boronic acid (41.82 g, 77.82 mmol), and then, 24.80 g (yield: 70%) of the product was obtained by the same method as in synthesis of Sub 2-3.
  • Synthesis of Sub 2-50
  • Figure US20220278285A1-20220901-C00222
  • After dibenzofuran, 1-bromo-8-phenyl-(CAS Registry Number: 1822310-20-2) (45 g, 139.24 mmol) were dissolved in THF (580 ml), the temperature of the reactant was lowered to −78° C. Thereafter, n-BuLi (2.5M in hexane) (13.38 g, 208.86 mmol) was added slowly thereto and the mixture was stirred at 0° C. for 1 hour. Thereafter, the temperature of the reactant was lowered to −78° C., triisopropyl borate (31.42 g, 167.08 mmol) and water (290 ml) were added thereto and the mixture was stirred at room temperature for 12 hour. When reaction was completed, the organic layer was dried with MgSO4 and concentrated. The concentrate was applied to silica gel column and recrystallized to obtain 26.88 g (yield: 67%) of the product.
  • The compound belonging to Sub 2 may be, but not limited to, the following compounds, and Table 2 shows FD-MS values of compounds belonging to Sub 2.
  • Figure US20220278285A1-20220901-C00223
    Figure US20220278285A1-20220901-C00224
    Figure US20220278285A1-20220901-C00225
    Figure US20220278285A1-20220901-C00226
    Figure US20220278285A1-20220901-C00227
    Figure US20220278285A1-20220901-C00228
    Figure US20220278285A1-20220901-C00229
    Figure US20220278285A1-20220901-C00230
    Figure US20220278285A1-20220901-C00231
    Figure US20220278285A1-20220901-C00232
  • TABLE 2
    Compound FD-MS Compound FD-MS
    Sub 2-1 m/z = 288.10 (C18H13BO3 = 288.11) Sub 2-3 m/z = 364.13 (C24H17BO3 = 364.21)
    Sub 2-5 m/z = 388.13 (C26H17BO3 = 388.23) Sub 2-6 m/z = 313.09 (C19H12BNO3 = 313.12)
    Sub 2-7 m/z = 455.14 (C28H18BN3O3 = 455.28) Sub 2-8 m/z = 340.10 (C20H13BN2O3 = 340.15)
    Sub 2-9 m/z = 338.11 (C22H15BO3 = 338.17) Sub 2-11 m/z = 416.13 (C26H17BN2O3 = 416.24)
    Sub 2-13 m/z = 404.16 (C27H21BO3 = 404.27) Sub 2-17 m/z = 466.15 (C30H19BN2O3 = 466.30)
    Sub 2-20 m/z = 366.12 (C22H15BN2O3 = 366.18) Sub 2-30 m/z = 380.10 (C24H17BO2S = 380.27)
    Sub 2-38 m/z = 365.12 (C23H16BNO3 = 365.20) Sub 2-39 m/z = 440.13 (C28H17BN2O3 = 440.27)
    Sub 2-40 m/z = 454.12 (C30H19BO2S = 454.35) Sub 2-42 m/z = 354.09 (C22H15BO2S = 354.23)
    Sub 2-45 m/z = 430.12 (C28H19BO2S = 430.33) Sub 2-46 m/z = 388.13 (C26H17BO3 = 388.23)
    Sub 2-47 m/z = 365.12 (C23H16BNO3 = 365.20) Sub 2-49 m/z = 293.13 (C18H8D5BO3 = 293.14)
    • 3. Synthesis Example of Final Product
  • Synthesis of Compound 1-3
  • Figure US20220278285A1-20220901-C00233
  • After Sub 1-1 (60 g, 133.35 mmol) in a round bottom flask was dissolved in THF (489 mL), Sub 2-3 (58.28 g, 160.01 mmol), Pd(PPh3)4 (6.16 g, 5.33 mmol), K2CO3 (55.29 g, 400.04 mmol) and water (244 mL) were added thereto and the mixture was stirred under reflux. When reaction was completed, the product was extracted with ether and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was applied to silica gel column and recrystallized to obtain 73.40 g (yield: 75%) of the product.
  • Synthesis of Compound 1-6
  • Figure US20220278285A1-20220901-C00234
  • THF (418 mL), Sub 2-1 (39.43 g, 136.87 mmol), Pd(PPh3)4 (5.27 g, 4.56 mmol), K2CO3 (47.29 g, 342.17 mmol), water (209 mL) were added to Sub 1-3 (60 g, 114.06 mmol), and then 61.11 g (yield: 73%) of the product was obtained by the same method as in synthesis of 1-3.
  • Synthesis of Compound 1-11
  • Figure US20220278285A1-20220901-C00235
  • THF (382 mL), Sub 2-6 (39.13 g, 124.98 mmol), Pd(PPh3)4 (4.81 g, 4.17 mmol), K2CO3 (43.18 g, 312.44 mmol) and water (191 mL) were added to Sub 1-6 (60 g, 104.15 mmol), and then 54.76 g (yield: 65%) of the product was obtained by the same method as in synthesis of 1-3.
  • Synthesis of Compound 1-14
  • Figure US20220278285A1-20220901-C00236
  • THF (404 mL), Sub 2-1 (288.11 g, 132.10 mmol), Pd(PPh3)4 (5.09 g, 4.40 mmol), K2CO3 (45.64 g, 330.26 mmol) and water (202 mL) were added to Sub 1-8 (60 g, 110.09 mmol), and then 52.21 g (yield: 63%) of the product was obtained by the same method as in synthesis of 1-3.
  • Synthesis of Compound 1-22
  • Figure US20220278285A1-20220901-C00237
  • THF (381 mL), Sub 2-1 (35.88 g, 124.55 mmol), Pd(PPh3)4 (4.80 g, 4.15 mmol), K2CO3 (43.03 g, 311.37 mmol) and water (190 mL) were added to Sub 1-15 (60 g, 103.79 mmol), and then 55.47 g (yield: 68%) of the product was obtained by the same method as in synthesis of 1-3.
  • Synthesis of Compound 1-44
  • Figure US20220278285A1-20220901-C00238
  • THF (410 mL), Sub 2-1 (38.62 g, 134.05 mmol), Pd(PPh3)4 (5.16 g, 4.47 mmol), K2CO3 (46.32 g, 335.13 mmol) and water (205 mL) were added to Sub 1-27 (60 g, 111.71 mmol), and then 49.93 g (yield: 60%) of the product was obtained by the same method as in synthesis of 1-3.
  • Synthesis of Compound 1-74
  • Figure US20220278285A1-20220901-C00239
  • THF (359 mL), Sub 2-26 (35.78 g, 117.63 mmol), Pd(PPh3)4 (4.53 g, 3.92 mmol), K2CO3 (40.64 g, 294.07 mmol) and water (180 mL) were added to Sub 1-50 (60 g, 98.02 mmol), and then 46.71 g (yield: 57%) of the product was obtained by the same method as in synthesis of 1-3.
  • Synthesis of Compound 1-98
  • Figure US20220278285A1-20220901-C00240
  • THF (484 mL), Sub 2-1 (45.59 g, 158.25 mmol), Pd(PPh3)4 (6.10 g, 5.27 mmol), K2CO3 (54.68 g, 395.61 mmol) and water (242 mL) were added to Sub 1-67 (60 g, 131.87 mmol), and then 70.80 g (yield: 81%) of the product was obtained by the same method as in synthesis of 1-3.
  • Synthesis of Compound 2-15
  • Figure US20220278285A1-20220901-C00241
  • THF (489 mL), (8-phenyldibenzo[b,d]furan-1-yl)boronic acid (46.10 g, 160.01 mmol), Pd(PPh3)4 (6.16 g, 5.33 mmol), K2CO3 (55.29 g, 400.04 mmol) and water (244 mL) were added to Sub 1-1 (60 g, 133.35 mmol), and then 58.77 g (yield: 67%) of the product was obtained by the same method as in synthesis of 1-3.
  • Synthesis of Compound 3-22
  • Figure US20220278285A1-20220901-C00242
  • THE (424 mL), (7-phenyldibenzo[b,d]furan-2-yl)boronic acid (39.97 g, 138.73 mmol), Pd(PPh3)4 (5.34 g, 4.62 mmol), K2CO3 (47.94 g, 346.83 mmol) and water (212 mL) were added to 2-chloro-4-(3-fluoronaphthalen-1-yl)-6-(7-(pyridin-3-yl)dibenzo[b,d]thiophen-3-yl)-1,3,5-triazine (60 g, 115.61 mmol), and then 51.26 g (yield: 61%) of the product was obtained by the same method as in synthesis of 1-3.
  • Synthesis of Compound 4-11
  • Figure US20220278285A1-20220901-C00243
  • THF (382 mL), (6-phenylnaphtho[2,3-b]benzofuran-2-yl)boronic acid (42.26 g, 124.98 mmol), Pd(PPh3)4 (4.81 g, 4.17 mmol), K2CO3 (43.18 g, 312.44 mmol) and water (191 mL) were added to Sub 1-70 (60 g, 104.15 mmol), and then 50.38 g (yield: 58%) of the product was obtained by the same method as in synthesis of 1-3.
  • Synthesis of Compound 4-38
  • Figure US20220278285A1-20220901-C00244
  • THF (85 mL), (8-([1,1′-biphenyl]-3-yl)dibenzo[b,d]thiophen-1-yl)boronic acid (10.52 g, 27.7 mmol), Pd(PPh3)4 (1.33 g, 1.2 mmol), K2CO3 (9.56 g, 69.1 mmol) and water (42 mL) were added to 2-chloro-4-phenyl-6-(6-phenyldibenzo[b,d]furan-4-yl)-1,3,5-triazine (10 g, 23.0 mmol), and then 14.38 g (yield: 85%) of the product was obtained by the same method as in synthesis of 1-3.
  • Synthesis of Compound 4-41
  • Figure US20220278285A1-20220901-C00245
  • THF (180 mL), (7-phenyldibenzo[b,d]furan-3-yl)boronic acid (16.9 g, 58.7 mmol), Pd(PPh3)4 (2.82 g, 2.4 mmol), K2CO3 (20.27 g, 146.7 mmol) and water (90 mL) were added to 2-chloro-4-phenyl-6-(6-phenyldibenzo[b,d]thiophen-4-yl)-1,3,5-triazine (22 g, 48.9 mmol), and then 25.73 g (yield: 80%) of the product was obtained by the same method as in synthesis of 1-3.
  • Synthesis of Compound 4-43
  • Figure US20220278285A1-20220901-C00246
  • THF (285 mL), (8-phenyldibenzo[b,d]furan-1-yl)boronic acid (26.89 g, 93.3 mmol), Pd(PPh3)4 (4.49 g, 3.9 mmol), K2CO3 (32.25 g, 233.4 mmol) and water (143 mL) were added to 2-chloro-4-phenyl-6-(6-phenyldibenzo[b,d]thiophen-3-yl)-1,3,5-triazine (35 g, 77.8 mmol), and then 36.84 g (yield: 72%) of the product was obtained by the same method as in synthesis of 1-3.
  • The FD-MS values of the compounds represented by Formula 1 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.
  • TABLE 3
    Compound FD-MS Compound FD-MS
    1-1 m/z = 657.19 (C45H27N3OS = 657.79) 1-2 m/z = 733.22 (C51H31N3OS = 733.89)
    1-3 m/z = 733.22 (C51H31N3OS = 733.89) 1-4 m/z = 733.22 (C51H31N3OS = 733.89)
    1-7 m/z = 707.20 (C49H29N3OS = 707.85) 1-8 m/z = 757.22 (C53H31N3OS = 757.91)
    1-9 m/z = 859.27 (C61H37N3OS = 860.05) 1-10 m/z = 707.20 (C49H29N3OS = 707.85)
    1-11 m/z = 808.23 (C56H32N4OS = 808.96) 1-12 m/z = 890.31 (C63H34D5N3OS = 891.12)
    1-13 m/z = 824.24 (C35H32N6OS = 824.96) 1-14 m/z = 752.20 (C50H29FN4OS = 752.87)
    1-15 m/z = 765.26 (C51H35N5OS = 765.94) 1-16 m/z = 765.17 (C49H27N5OS2 = 765.91)
    1-17 m/z = 807.23 (C57H33N3OS = 807.97) 1-18 m/z = 833.25 (C59H35N3OS = 834.01)
    1-19 m/z = 733.22 (C51H31N3OS = 733.89) 1-20 m/z = 733.22 (C51H31N3OS = 733.89)
    1-21 m/z = 783.23 (C55H33N3OS = 783.95) 1-22 m/z = 785.22 (C53H31N5OS = 785.93)
    1-23 m/z = 859.27 (C61H37N3OS = 860.05) 1-24 m/z = 785.22 (C53H31N5OS = 785.93)
    1-25 m/z = 809.22 (C55H31N5OS = 809.95) 1-26 m/z = 849.28 (C60H39N3OS = 850.05)
    1-27 m/z = 783.23 (C55H33N3OS = 783.95) 1-28 m/z = 657.19 (C45H27N3OS = 657.79)
    1-29 m/z = 809.25 (C57H35N3OS = 809.99) 1-32 m/z = 900.27 (C61H36N6OS = 901.06)
    1-33 m/z = 835.24 (C57H33N5OS = 835.99) 1-34 m/z = 901.25 (C61H35N5O2S = 902.04)
    1-35 m/z = 809.25 (C37H33N3OS = 809.99) 1-36 m/z = 938.21 (C59H31F5N4OS = 938.98)
    1-37 m/z = 783.23 (C55H33N3OS = 783.95) 1-42 m/z = 812.24 (C54H32N6OS = 812.95)
    1-43 m/z = 950.31 (C67H42N4OS = 951.16) 1-44 m/z = 744.21 (C49H24D5N3OS2 = 744.94)
    1-50 m/z = 726.19 (C48H27FN4OS = 726.83) 1-51 m/z = 791.27 (C53H37N5OS = 791.97)
    1-58 m/z = 897.28 (C64H39N3OS = 898.10) 1-59 m/z = 822.25 (C57H34N4OS = 822.99)
    1-60 m/z = 887.27 (C61H37N5OS = 888.06) 1-64 m/z = 885.28 (C63H39N3OS = 886.09)
    1-68 m/z = 911.27 (C63H37N5OS = 912.08) 1-69 m/z = 885.26 (C61H35N5OS = 886.05)
    1-70 m/z = 989.25 (C69H39N3OS2 = 990.21) 1-75 m/z = 909.28 (C65H39N3OS = 910.11)
    1-76 m/z = 856.23 (C57H36N4OS2 = 857.06) 1-78 m/z = 929.32 (C65H35D5N4OS = 930.15)
    1-79 m/z = 735.21 (C49H29N5OS = 735.87) 1-90 m/z = 784.23 (C54H32N4OS = 784.94)
    1-92 m/z = 889.28 (C62H39N3O2S = 890.07) 1-96 m/z = 888.27 (C60H36N6OS = 889.05)
    1-98 m/z = 662.22 (C45H22D5N3OS = 662.82) 1-99 m/z = 667.25 (C45H17D10N3OS = 667.85)
    1-100 m/z = 733.22 (C51H31N3OS = 733.89) 2-15 m/z = 657.19 (C45H27N3OS = 657.79)
    • Synthesis Example 2
  • As shown in Reaction Schemes 4-1 and 4-2 below, the compound represented by Formula 12 according to the present invention can be synthesized by reacting Sub with Sub 4-1, but there is no limitation thereto.
  • <Reaction Scheme 4-1> (where L2 in Formula 12 is not a single bond)
  • Figure US20220278285A1-20220901-C00247
  • Figure US20220278285A1-20220901-C00248
  • Synthesis of Compound 5-1
  • Figure US20220278285A1-20220901-C00249
  • After 3-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) was dissolved in THF, (9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazol-3-yl)boronic acid (8.8 g, 20 mmol), Pd(PPh3)4 (0.03 eq.), K2CO3 (3 eq.) and water were added thereto and the mixture was stirred under reflux. When reaction was completed, the product was extracted with ether and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was applied to silica gel column and recrystallized to obtain 9.2 g (yield: 72%) of the product.
  • Synthesis of Compound 5-21
  • Figure US20220278285A1-20220901-C00250
  • Dibenzo[b,d]furan-2-ylboronic acid (4.2 g, 20 mmol) were added to 10-bromo-7-(pyridin-2-yl)-7H-benzo[c]carbazole (7.5 g, 20 mmol), and then 6.5 g (yield: 71%) of the product was obtained by the same method as in synthesis of 5-1.
  • Synthesis of Compound 5-25
  • Figure US20220278285A1-20220901-C00251
  • (9-(naphthalen-2-yl)-9H-carbazol-3-yl)boronic acid (6.7 g, 20 mmol) were added to 9-([1,1′-biphenyl]-4-yl)-3-bromo-9H-carbazole (8.0 g, 20 mmol), and then 9.2 g (yield: 75%) of the product was obtained by the same method as in synthesis of 5-1.
  • Synthesis of Compound 5-31
  • Figure US20220278285A1-20220901-C00252
  • (9-phenyl-9H-carbazol-3-yl)boronic acid (5.7 g, 20 mmol) were added to 3′-bromo-9-phenyl-9H-2,9′-bicarbazole (9.7 g, 20 mmol), and then 9.5 g (yield: 73%) of the product was obtained by the same method as in synthesis of 5-1.
  • Synthesis of Compound 5-32
  • Figure US20220278285A1-20220901-C00253
  • (12-([1,1′:4′,1″-terphenyl]-4-yl)-12H-benzo[4,5]thieno[2,3-a]carbazol-3-yl)boronic acid (10.9 g, 20 mmol) were added to 3-bromo-9-(dibenzo[b,d]furan-2-yl)-9H-carbazole (8.2 g, 20 mmol), and then 11.5 g (yield: 69%) of the product was obtained by the same method as in synthesis of 5-1.
  • Synthesis of Compound 5-34
  • Figure US20220278285A1-20220901-C00254
  • (4-(dibenzo[b,d]thiophen-3-yl)phenyl)boronic acid (6.1 g, 20 mmol) were added to 4-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol), and then 6.7 g (yield: 67%) of the product was obtained by the same method as in synthesis of 5-1.
  • Synthesis of Compound 5-35
  • Figure US20220278285A1-20220901-C00255
  • 9(9,9-dimethyl-9H-fluoren-3-yl)boronic acid (4.8 g, 20 mmol) were added to 3-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol), and then 6.1 g (yield: 70%) of the product was obtained by the same method as in synthesis of 5-1.
  • The FD-MS values of the compounds according to Formula 1 of the present invention prepared according to the above synthesis examples are shown in the following Table 4.
  • TABLE 4
    Compound FD-MS Compound FD-MS
    5-1 m/z = 639.24 (C45H29N5 = 639.75) 5-2 m/z = 715.27 (C51H33N5 = 715.84)
    5-3 m/z = 780.33 (C57H40N4 = 780.95) 5-4 m/z = 639.24 (C45H29N5 = 639.75)
    5-5 m/z = 715.27 (C51H33N5 = 715.84) 5-6 m/z = 780.33 (C57H40N4 = 780.95)
    5-7 m/z = 612.23 (C44H28N4 = 612.72) 5-8 m/z = 612.23 (C44H28N4 = 612.72)
    5-9 m/z = 662.25 (C48H30N4 = 662.78) 5-10 m/z = 484.19 (C36H24N2 = 484.59)
    5-11 m/z = 639.24 (C45H29N5 = 639.75) 5-12 m/z = 715.27 (C51H33N5 = 715.84)
    5-13 m/z = 715.27 (C51H33N5 = 715.84) 5-14 m/z = 638.25 (C46H30N4 = 638.76)
    5-15 m/z = 579.18 (C40H25N3S = 579.71) 5-16 m/z = 410.14 (C29H18N2S = 410.47)
    5-17 m/z = 486.17 (C35H22N2O = 486.56) 5-18 m/z = 486.17 (C35H22N2O = 486.56)
    5-19 m/z = 486.17 (C35H22N2O = 486.56) 5-20 m/z = 563.20 (C40H25N3O = 563.65)
    5-21 m/z = 460.16 (C33H20N2O = 460.52) 5-22 m/z = 536.19 (C39H24N2O = 536.62)
    5-23 m/z = 689.26 (C49H31N5 = 689.80) 5-24 m/z = 585.22 (C43H27N3 = 585.69)
    5-25 m/z = 610.24 (C46H30N2 = 610.76) 5-26 m/z = 610.24 (C46H30N2 = 610.76)
    5-27 m/z = 636.26 (C48H32N2 = 636.80) 5-28 m/z = 636.26 (C48H32N2 = 636.80)
    5-29 m/z = 610.24 (C46H30N2 = 610.76) 5-30 m/z = 610.24 (C46H30N2 = 610.76)
    5-31 m/z = 649.25 (C48H31N3 = 649.80) 5-32 m/z = 832.25 (C60H36N2OS = 833.02)
    5-33 m/z = 560.23 (C42H28N2 = 560.70) 5-34 m/z = 501.16 (C36H23NS = 501.65)
    5-35 m/z = 435.20 (C33H25N = 435.57) 5-36 m/z = 725.28 (C54H35N3 = 725.90)
    5-37 m/z = 650.24 (C48H30N2O = 650.78) 5-38 m/z = 650.24 (C48H30N2O = 650.78)
    5-39 m/z = 650.24 (C48H30N2O = 650.78) 5-40 m/z = 650.24 (C48H30N2O = 650.78)
    5-41 m/z = 666.21 (C48H30N2S = 666.84) 5-42 m/z = 666.21 (C48H30N2S = 666.84)
    5-43 m/z = 666.21 (C48H30N2S = 666.84) 5-44 m/z = 666.21 (C48H30N2S = 666.84)
    5-45 m/z = 650.24 (C48H30N2O = 650.78) 5-46 m/z = 650.24 (C48H30N2O = 650.78)
    5-47 m/z = 650.24 (C48H30N2O = 650.78) 5-48 m/z = 650.24 (C48H30N2O = 650.78)
    5-49 m/z = 666.21 (C48H30N2S = 666.84) 5-50 m/z = 666.21 (C48H30N2S = 666.84)
    5-51 m/z = 666.21 (C48H30N2S = 666.84) 5-52 m/z = 666.21 (C48H30N2S = 666.84)
    5-57 m/z = 636.26 (C48H32N2 = 636.80) 5-58 m/z = 725.28 (C54H35N3 = 725.90)
    • Synthesis Example 3
  • The compound represented by Formula 20 according to the present invention can be synthesized as follows, but is not limited thereto.
  • Synthesis of Compound 13-17
  • Figure US20220278285A1-20220901-C00256
  • After 9-(4′-bromo-[1,1′-biphenyl]-4-yl)-9H-carbazole(9.6 g, 24 mmol) was dissolved in toluene, di([1,1′-biphenyl]-4-yl)amine(6.4 g, 20 mmol), Pd2(dba)3 (0.05 eq.), PPh3 (0.1 eq.) and NaOt-Bu (3 eq.) were added thereto and the mixture was stirred under reflux at 100° C. for 24. When reaction was completed, the product was extracted with ether and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was applied to silica gel column and recrystallized to obtain 12.9 g (yield: 84%) of the product.
  • Synthesis of Compound 13-32
  • Figure US20220278285A1-20220901-C00257
  • After 3-(4-bromophenyl)-9-phenyl-9H-carbazole (9.6 g, 24 mmol) was dissolved in toluene, N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (7.2 g, 20 mmol), Pd2(dba)3 (0.05 eq.), PPh3 (0.1 eq.) and NaOt-Bu (3 eq.) were added thereto and then 13.8 g (yield: 85%) of the product was obtained by the same method as in synthesis of 13-17.
  • Synthesis of Compound 14-34
  • Figure US20220278285A1-20220901-C00258
  • After Sub 5(4) (4.7 g, 20 mmol), Pd2(dba)3 (0.5 g, 0.6 mmol), P(t-Bu)3 (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were added to Sub 4(19) (9.5 g, mmol) and the reaction was carried out at 100° C. When reaction was completed, the product was extracted with CH2Cl2 and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was applied to silica gel column and recrystallized to obtain 9.8 g (yield: 78%) of the product.
  • Synthesis of Compound 14-58
  • Figure US20220278285A1-20220901-C00259
  • Sub 5(7) (5.7 g, 20 mmol), Pd2(dba)3 (0.5 g, 0.6 mmol), P(t-Bu)3 (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were added to Sub 4(35) (8.4 g, 20 mmol), and then 10.4 g (yield: 83%) of the product was obtained by the same method as in synthesis of 14-34.
  • Synthesis of Compound 14-59
  • Figure US20220278285A1-20220901-C00260
  • Sub 5(11) (7.9 g, 20 mmol), Pd2(dba)3 (0.5 g, 0.6 mmol), P(t-Bu)3 (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were added to Sub 4(32) (12.9 g, mmol), and then 5.2 g (yield: 79%) of the product was obtained by the same method as in synthesis of 14-34.
  • Synthesis of Compound 14-69
  • Figure US20220278285A1-20220901-C00261
  • 4-(0∥p (0.5 g, 0.6 mmol), P(t-Bu)3 (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were added to N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (7.2 g, 20 mmol), and then 12.2 g (yield: 81%) of the product was obtained by the same method as in synthesis of 14-34.
  • Synthesis of Compound 14-71
  • Figure US20220278285A1-20220901-C00262
  • N-(3-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine (10.6 g, 20 mmol), Pd2(dba)3 (0.5 g, 0.6 mmol), P(t-Bu)3 (0.2 g, 2 mmol), t-BuONa (5.8 g, mmol) and toluene (300 mL) were added to N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine (7.5 g, 20 mmol), and then 12.9 g (yield: 78%) of the product was obtained by the same method as in synthesis of 14-34.
  • Synthesis of Compound 14-72
  • Figure US20220278285A1-20220901-C00263
  • 2-bromo-9,9-dimethyl-9H-fluorene (5.5 g, 20 mmol), Pd2(dba)3 (0.5 g, 0.6 mmol), P(t-Bu)3 (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were added to N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)dibenzo[b,d]furan-1-amine (10.0 g, 20 mmol), and then 11.1 g (yield: 80%) of the product was obtained by the same method as in synthesis of 14-34.
    • Synthesis Example 4
  • As shown in Reaction Scheme 5 below, the compound represented by Formula A according to the present invention can be synthesized by reacting Sub a with Sub b, but there is no limitation thereto.
  • Figure US20220278285A1-20220901-C00264
    • Synthesis Example of Sub a
  • Sub a of the Reaction Scheme 5 can be synthesized according to the reaction route of the following Reaction Scheme 5-1, but there is no limitation thereto.
  • Figure US20220278285A1-20220901-C00265
  • Figure US20220278285A1-20220901-C00266
  • 1-bromo-3-chlorobenzene (50 g, 261.2 mmol), N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine (125.92 g, 391.7 mmol), Pd2(dba)3 (7.17 g, 7.8 mmol), P(t-Bu)3 (4.23 g, 20.9 mmol), NaO(t-Bu) (75.30 g, 783.5 mmol) and toluene (3200 mL) were placed in a round bottom flask and then the mixture was heated under reflux at 80° C. for 4 hours. When the reaction is completed, the resultant was diluted with distilled water at room temperature and was extracted with CH2Cl2 and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was recrystallized with methylene chloride and hexane to obtain Sub a-3 (93.63 g, 83%) of the product.
  • Synthesis of Sub a-29
  • Figure US20220278285A1-20220901-C00267
  • 1-Bromo-3-chlorobenzene (50 g, 261.2 mmol), N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine (147.09 g, 391.7 mmol), Pd2(dba)3 (7.17 g, 7.8 mmol), P(t-Bu)3 (4.23 g, 20.9 mmol), NaO(t-Bu) (75.30 g, 783.5 mmol) and toluene (3200 mL) were placed in a round bottom flask and then the mixture was heated under reflux at 80° C. for 4 hours. When the reaction is completed, the resultant was diluted with distilled water at room temperature and was extracted with CH2Cl2 and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was recrystallized with methylene chloride and hexane to obtain Sub a-29 (107.89 g, 85%) of the product.
  • Synthesis of Sub a-39
  • Figure US20220278285A1-20220901-C00268
  • 4-Bromo-4′-chloro-1,1′-biphenyl (50 g, 186.9 mmol), N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-4-amine (105.25 g, 280.3 mmol), Pd2(dba)3 (5.13 g, 5.6 mmol), P(t-Bu)3 (3.02 g, 15.0 mmol), NaO(t-Bu) (53.88 g, 560.6 mmol) and toluene (2300 mL) were placed in a round bottom flask and then the mixture was heated under reflux at 80° C. for 4 hours. When the reaction is completed, the resultant was diluted with distilled water at room temperature and was extracted with CH2Cl2 and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was recrystallized with methylene chloride and hexane to obtain Sub a-39 (87.19 g, 83%) of the product.
  • The example of the compound belonging to Sub a may be, but not limited to, the following compounds, and Table 5 shows ED-MS values of the following compounds.
  • Figure US20220278285A1-20220901-C00269
    Figure US20220278285A1-20220901-C00270
    Figure US20220278285A1-20220901-C00271
    Figure US20220278285A1-20220901-C00272
    Figure US20220278285A1-20220901-C00273
    Figure US20220278285A1-20220901-C00274
    Figure US20220278285A1-20220901-C00275
    Figure US20220278285A1-20220901-C00276
    Figure US20220278285A1-20220901-C00277
    Figure US20220278285A1-20220901-C00278
    Figure US20220278285A1-20220901-C00279
    Figure US20220278285A1-20220901-C00280
    Figure US20220278285A1-20220901-C00281
    Figure US20220278285A1-20220901-C00282
    Figure US20220278285A1-20220901-C00283
    Figure US20220278285A1-20220901-C00284
    Figure US20220278285A1-20220901-C00285
    Figure US20220278285A1-20220901-C00286
    Figure US20220278285A1-20220901-C00287
    Figure US20220278285A1-20220901-C00288
    Figure US20220278285A1-20220901-C00289
    Figure US20220278285A1-20220901-C00290
    Figure US20220278285A1-20220901-C00291
    Figure US20220278285A1-20220901-C00292
    Figure US20220278285A1-20220901-C00293
    Figure US20220278285A1-20220901-C00294
    Figure US20220278285A1-20220901-C00295
    Figure US20220278285A1-20220901-C00296
    Figure US20220278285A1-20220901-C00297
    Figure US20220278285A1-20220901-C00298
    Figure US20220278285A1-20220901-C00299
  • TABLE 5
    Compound FD-MS Compound FD-MS
    Sub a-1 m/z = 279.08 (C18H14ClN = 279.77) Sub a-2 m/z = 355.11 (C24H18ClN = 355.87)
    Sub a-3 m/z = 431.14 (C30H22ClN = 431.96) Sub a-4 m/z = 507.18 (C36H26ClN = 508.06)
    Sub a-5 m/z = 507.18 (C36H26ClN = 508.06) Sub a-6 m/z = 329.10 (C22H16ClN = 329.83)
    Sub a-7 m/z = 405.13 (C28H20ClN = 405.93) Sub a-8 m/z = 395.14 (C27H22ClN = 395.93)
    Sub a-9 m/z = 471.18 (C33H26ClN = 472.03) Sub a-10 m/z = 471.18 (C33H26ClN = 472.03)
    Sub a-11 m/z = 511.21 (C36H30ClN = 512.09) Sub a-12 m/z = 471.18 (C33H26ClN = 472.03)
    Sub a-13 m/z = 471.18 (C33H26ClN = 472.03) Sub a-14 m/z = 511.21 (C36H30ClN = 512.09)
    Sub a-15 m/z = 595.21 (C43H30ClN = 596.17) Sub a-16 m/z = 635.24 (C46H34ClN = 636.24)
    Sub a-17 m/z = 519.18 (C37H26ClN = 520.07) Sub a-18 m/z = 595.21 (C43H30ClN = 596.17)
    Sub a-19 m/z = 671.24 (C49H34ClN = 672.27) Sub a-20 m/z = 519.18 (C37H26ClN = 520.07)
    Sub a-21 m/z = 593.19 (C43H28ClN = 594.15) Sub a-22 m/z = 595.21 (C43H30ClN = 596.17)
    Sub a-23 m/z = 671.24 (C49H34ClN = 672.27) Sub a-24 m/z = 635.24 (C46H34ClN = 636.24)
    Sub a-25 m/z = 595.21 (C43H30ClN = 596.17) Sub a-26 m/z = 369.09 (C24H16ClNO = 369.85)
    Sub a-27 m/z = 445.12 (C30H20ClNO = 445.95) Sub a-28 m/z = 445.12 (C30H20ClNO = 445.95)
    Sub a-29 m/z = 485.15 (C33H24ClNO = 486.01) Sub a-30 m/z = 609.19 (C43H28ClNO = 610.15)
    Sub a-31 m/z = 369.09 (C24H16ClNO = 369.85) Sub a-32 m/z = 419.11 (C28H18ClNO = 419.91)
    Sub a-33 m/z = 609.19 (C43H28ClNO = 610.15) Sub a-34 m/z = 445.12 (C30H20ClNO = 445.95)
    Sub a-35 m/z = 445.12 (C30H20ClNO = 445.95) Sub a-36 m/z = 495.14 (C34H22ClNO = 496.01)
    Sub a-37 m/z = 485.15 (C33H24ClNO = 486.01) Sub a-38 m/z = 369.09 (C24H16ClNO = 369.85)
    Sub a-39 m/z = 561.1 (C39H28ClNO = 562.11) Sub a-40 m/z = 461.10 (C30H20ClNS = 462.01)
    Sub a-41 m/z = 577.16 (C39H28ClNS = 578.17) Sub a-42 m/z = 461.10 (C30H20ClNS = 462.01)
    Sub a-43 m/z = 435.08 (C28H18ClNS = 435.97) Sub a-44 m/z = 501.13 (C33H24ClNS = 502.07)
    Sub a-45 m/z = 385.07 (C24H16ClNS = 385.91) Sub a-46 m/z = 625.16 (C43H28ClNS = 626.21)
    Sub a-47 m/z = 431.14 (C30H22ClN = 431.96) Sub a-48 m/z = 355.11 (C24H18ClN = 355.87)
    Sub a-49 m/z = 507.18 (C36H26ClN = 508.06) Sub a-50 m/z = 405.13 (C28H20ClN = 405.93)
    Sub a-51 m/z = 547.21 (C39H30ClN = 548.13) Sub a-52 m/z = 395.14 (C27H22ClN = 395.93)
    Sub a-53 m/z = 561.22 (C40H32ClN = 562.15) Sub a-54 m/z = 759.27 (C56H38ClN = 760.38)
    Sub a-55 m/z = 671.24 (C49H34ClN = 672.27) Sub a-56 m/z = 419.11 (C28H18ClNO = 419.91)
    Sub a-57 m/z = 609.19 (C43H28ClNO = 610.15) Sub a-58 m/z = 369.09 (C24H16ClNO = 369.85)
    Sub a-59 m/z = 485.15 (C33H24ClNO = 486.01) Sub a-60 m/z = 445.12 (C30H20ClNO = 445.95)
    Sub a-61 m/z = 445.12 (C30H20ClNO = 445.95) Sub a-62 m/z = 435.08 (C28H18ClNS = 435.97)
    Sub a-63 m/z = 501.13 (C33H24ClNS = 502.07) Sub a-64 m/z = 461.10 (C30H20ClNS = 462.01)
    Sub a-65 m/z = 511.12 (C34H22ClNS = 512.07) Sub a-66 m/z = 431.14 (C30H22ClN = 431.96)
    Sub a-67 m/z = 569.19 (C41H28ClN = 570.13) Sub a-68 m/z = 485.15 (C33H24ClNO = 486.01)
    Sub a-69 m/z = 355.11 (C24H18ClN = 355.87) Sub a-70 m/z = 405.13 (C28H20ClN = 405.93)
    Sub a-71 m/z = 521.19 (C37H28ClN = 522.09) Sub a-72 m/z = 547.21 (C39H30ClN = 548.13)
    Sub a-73 m/z = 395.14 (C27H22ClN = 395.93) Sub a-74 m/z = 517.16 (C37H24ClN = 518.06)
    Sub a-75 m/z = 595.21 (C43H30ClN = 596.17) Sub a-76 m/z = 609.19 (C43H28ClNO = 610.15)
    Sub a-77 m/z = 485.15 (C33H24ClNO = 486.01) Sub a-78 m/z = 385.07 (C24H16ClNS = 385.91)
    Sub a-79 m/z = 577.16 (C39H28ClNS = 578.17) Sub a-80 m/z = 431.14 (C30H22ClN = 431.96)
    Sub a-81 m/z = 395.14 (C27H22ClN = 395.93) Sub a-82 m/z = 569.19 (C41H28ClN = 570.13)
    Sub a-83 m/z = : 485.15 (C33H24ClNO = 486.01) Sub a-84 m/z = 495.14 (C34H22ClNO = 496.01)
    Sub a-85 m/z = 501.13 (C33H24ClNS = 502.07) Sub a-86 m/z = 435.08 (C28H18ClNS = 435.97)
    Sub a-87 m/z = 547.21 (C39H30ClN = 548.13) Sub a-88 m/z = 519.18 (C37H26ClN = 520.07)
    Sub a-89 m/z = 595.21 (C43H30ClN = 596.17) Sub a-90 m/z = 609.19 (C43H28ClNO = 610.15)
    Sub a-91 m/z = 431.14 (C30H22ClN = 431.96) Sub a-92 m/z = 471.18 (C33H26ClN = 472.03)
    Sub a-93 m/z = 385.07 (C24H16ClNS = 385.91) Sub a-94 m/z = 431.14 (C30H22ClN = 431.96)
    Sub a-95 m/z = 329.10 (C22H16ClN = 329.83) Sub a-96 m/z = 471.18 (C33H26ClN = 472.03)
    Sub a-97 m/z = 501.13 (C33H24ClNS = 502.07) Sub a-98 m/z = 471.18 (C33H26ClN = 472.03)
    Sub a-99 m/z = 759.27 (C56H38ClN = 760.38) Sub a-100 m/z = 609.19 (C43H28ClNO = 610.15)
    Sub a-101 m/z = 360.14 (C24H13D5ClN = 360.90) Sub a-102 m/z = 405.13 (C28H20ClN = 405.93)
    Sub a-103 m/z = 471.18 (C33H26ClN = 472.03) Sub a-104 m/z = 519.18 (C37H26ClN = 520.07)
    Sub a-105 m/z = 609.19 (C43H28ClNO = 610.15) Sub a-106 m/z = 355.11 (C24H18ClN = 355.87)
    Sub a-107 m/z = 507.18 (C36H26ClN = 508.06) Sub a-108 m/z = 519.18 (C37H26ClN = 520.07)
    Sub a-109 m/z = 481.16 (C34H24ClN = 482.02) Sub a-110 m/z = 609.19 (C43H28ClNO = 610.15)
    Sub a-111 m/z = 445.12 (C30H20ClNO = 445.95) Sub a-112 m/z = 461.10 (C30H20ClNS = 462.01)
    Sub a-113 m/z = 429.13 (C30H20ClN = 429.95) Sub a-114 m/z = 379.11 (C26H18ClN = 379.89)
    Sub a-115 m/z = 519.18 (C37H26ClN = 520.07) Sub a-116 m/z = 635.24 (C46H34ClN = 636.24)
    Sub a-117 m/z = 445.12 (C30H20ClNO = 445.95) Sub a-118 m/z = 575.24 (C44H23ClN = 576.18)
    Sub a-119 m/z = 561.19 (C39H28ClNO = 562.11)
    • Synthesis Example of Sub b
  • Sub b of the Reaction Scheme 5 can be synthesized according to the reaction route of the following Reaction Scheme 5-2, but there is no limitation thereto.
  • Figure US20220278285A1-20220901-C00300
  • Synthesis of Sub b-1
  • Figure US20220278285A1-20220901-C00301
  • 9-(3-bromophenyl)-9-phenyl-9H-fluorene (100 g, 251.7 mmol), aniline (35.16 g, 377.5 mmol), Pd2(dba)3 (6.91 g, 7.6 mmol), P(t-Bu)3 (4.07 g, 20.1 mmol), NaO(t-Bu) (72.57 g, 755.1 mmol) and toluene (3150 mL) were placed in a round bottom flask and then the mixture was heated under reflux at 60° C. for 4 hours. When the reaction is completed, the resultant was diluted with distilled water at room temperature and was extracted with CH2Cl2 and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was recrystallized with methylene chloride and hexane to obtain Sub b-1 (82.46 g, 80%) of the product.
  • Synthesis of Sub b-17
  • Figure US20220278285A1-20220901-C00302
  • 9-(3-bromophenyl)-9-phenyl-9H-fluorene (100 g, 251.7 mmol), 9,9-dimethyl-9H-fluoren-3-amine (79.01 g, 377.5 mmol), Pd2(dba)3 (6.91 g, 7.6 mmol), P(t-Bu)3 (4.07 g, 20.1 mmol), NaO(t-Bu) (72.57 g, 755.1 mmol) and toluene (3150 mL) were placed in a round bottom flask and then the mixture was heated under reflux at 60° C. for 4 hours. When the reaction is completed, the resultant was diluted with distilled water at room temperature and was extracted with CH2Cl2 and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was recrystallized with methylene chloride and hexane to obtain Sub b-17 (101.88 g, 77%) of the product.
  • Synthesis of Sub b-26
  • Figure US20220278285A1-20220901-C00303
  • 9-(3-bromophenyl)-9-phenyl-9H-fluorene (100 g, 251.7 mmol), 9,9-dimethyl-9H-fluoren-4-amine (69.17 g, 377.5 mmol), Pd2(dba)3 (6.91 g, 7.6 mmol), P(t-Bu)3 (4.07 g, 20.1 mmol), NaO(t-Bu) (72.57 g, 755.1 mmol) and toluene (3150 mL) were placed in a round bottom flask and then the mixture was heated under reflux at 60° C. for 4 hours. When the reaction is completed, the resultant was diluted with distilled water at room temperature and was extracted with CH2Cl2 and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was recrystallized with methylene chloride and hexane to obtain Sub b-26 (99.34 g, 79%) of the product.
  • Example of the compounds belonging to Sub b may be, but not limited to, the following compounds, and Table 6 shows the FD-MS values of the following compounds.
  • Figure US20220278285A1-20220901-C00304
    Figure US20220278285A1-20220901-C00305
    Figure US20220278285A1-20220901-C00306
    Figure US20220278285A1-20220901-C00307
    Figure US20220278285A1-20220901-C00308
    Figure US20220278285A1-20220901-C00309
  • TABLE 6
    Compound FD-MS Compound FD-MS
    Sub b-1 m/z = 409.18 (C31H23N = 409.53) Sub b-2 m/z = 409.18 (C31H23N = 409.53)
    Sub b-3 m/z = 409.18 (C31H23N = 409.53) Sub b-4 m/z = 414.21 (C31H18D5N = 414.56)
    Sub b-5 m/z = 485.21 (C37H27N = 485.63) Sub b-6 m/z = 485.21 (C37H27N = 485.63)
    Sub b-7 m/z = 485.21 (C37H27N = 485.63) Sub b-8 m/z = 485.21 (C37H27N = 485.63)
    Sub b-9 m/z = 485.21 (C37H27N = 485.63) Sub b-10 m/z = 485.21 (C37H27N = 485.63)
    Sub b-11 m/z = 525.25 (C40H31N = 525.70) Sub b-12 m/z = 525.25 (C40H31N = 525.70)
    Sub b-13 m/z = 527.26 (C40H33N = 527.71) Sub b-14 m/z = 525.25 (C40H31N = 525.70)
    Sub b-15 m/z = 525.25 (C40H31N = 525.70) Sub b-16 m/z = 525.25 (C40H31N = 525.70)
    Sub b-17 m/z = 525.25 (C40H31N = 525.70) Sub b-18 m/z = 525.25 (C40H31N = 525.70)
    Sub b-19 m/z = 649.28 (C50H35N = 649.84) Sub b-20 m/z = 647.26 (C50H33N = 647.82)
    Sub b-21 m/z = 649.28 (C50H35N = 649.84) Sub b-22 m/z = 649.28 (C50H35N = 649.84)
    Sub b-23 m/z = 649.28 (C50H35N = 649.84) Sub b-24 m/z = 649.28 (C50H35N = 649.84)
    Sub b-25 m/z = 649.28 (C50H35N = 649.84) Sub b-26 m/z = 499.19 (C37H25NO = 499.61)
    Sub b-27 m/z = 549.21 (C41H27NO = 549.67) Sub b-28 m/z = 499.19 (C37H25NO = 499.61)
    Sub b-29 m/z = 499.19 (C37H25NO = 499.61) Sub b-30 m/z = 575.22 (C43H29NO = 575.71)
    Sub b-31 m/z = 575.22 (C43H29NO = 575.71) Sub b-32 m/z = 499.19 (C37H25NO = 499.61)
    Sub b-33 m/z = 437.18 (C32H23NO = 437.54)
    • Synthesis Example of Final Product
  • Synthesis of compound G-3
  • Figure US20220278285A1-20220901-C00310
  • Sub a-3 (10 g, 23.2 mmol), Sub b-1 (9.48 g, 23.2 mmol), Pd2(dba)3 (0.64 g, 0.7 mmol), P(t-Bu)3 (0.37 g, 1.9 mmol), NaO(t-Bu) (6.67 g, 69.5 mmol) and toluene (230 mL) were placed in a round bottom flask and then the mixture was heated under reflux at 110° C. for 3 hours. When the reaction is completed, the resultant was diluted with distilled water at room temperature and was extracted with CH2C2 and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was dissolved in toluene and filtered with a silica gel filter. After concentrating the filtered solution, the concentrate was recrystallized with toluene and acetone to obtain G-3 (17.0 g, 89%) of the product.
  • Synthesis of Compound G-29
  • Figure US20220278285A1-20220901-C00311
  • Sub a-29 (10 g, 20.6 mmol), Sub b-1 (8.43 g, 20.6 mmol), Pd2(dba)3 (0.57 g, 0.6 mmol), P(t-Bu)3 (0.33 g, 1.6 mmol), NaO(t-Bu) (5.93 g, 61.7 mmol) and toluene (210 mL) were placed in a round bottom flask and then the mixture was heated under reflux at 110° C. for 3 hours. When the reaction is completed, the resultant was diluted with distilled water at room temperature and was extracted with CH2Cl2 and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was dissolved in toluene and filtered with a silica gel filter. After concentrating the filtered solution, the concentrate was recrystallized with toluene and acetone to obtain G-29 (15.20 g, 86%) of the product.
  • Synthesis of Compound G-81
  • Figure US20220278285A1-20220901-C00312
  • Sub a-116 (10 g, 15.7 mmol), Sub b-8 (7.63 g, 15.7 mmol), Pd2(dba)3 (0.43 g, 0.5 mmol), P(t-Bu)3 (0.25 g, 1.3 mmol), NaO(t-Bu) (4.53 g, 47.2 mmol) and toluene (160 mL) were placed in a round bottom flask and then the mixture was heated under reflux at 110° C. for 3 hours. When the reaction is completed, the resultant was diluted with distilled water at room temperature and was extracted with CH2Cl2 and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was dissolved in toluene and filtered with a silica gel filter. After concentrating the filtered solution, the concentrate was recrystallized with toluene and acetone to obtain G-81 (13.99 g, 82%) of the product.
  • Synthesis of Compound G-88
  • Figure US20220278285A1-20220901-C00313
  • Sub a-69 (10 g, 28.1 mmol), Sub b-12 (14.77 g, 28.1 mmol), Pd2(dba)3 (0.77 g, 0.8 mmol), P(t-Bu)3 (0.45 g, 2.2 mmol), NaO(t-Bu) (8.10 g, 84.3 mmol) and toluene (280 mL) were placed in a round bottom flask and then the mixture was heated under reflux at 110° C. for 3 hours. When the reaction is completed, the resultant was diluted with distilled water at room temperature and was extracted with CH2Cl2 and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was dissolved in toluene and filtered with a silica gel filter. After concentrating the filtered solution, the concentrate was recrystallized with toluene and acetone to obtain G-88 (19.47 g, 82%) of the product.
  • Synthesis of Compound G-137
  • Figure US20220278285A1-20220901-C00314
  • Sub a-90 (10 g, 16.4 mmol), Sub b-21 (10.65 g, 16.4 mmol), Pd2(dba)3 (0.45 g, 0.5 mmol), P(t-Bu)3 (0.27 g, 1.3 mmol), NaO(t-Bu) (4.73 g, 49.2 mmol) and toluene (170 mL) were placed in a round bottom flask and then the mixture was heated under reflux at 110° C. for 3 hours. When the reaction is completed, the resultant was diluted with distilled water at room temperature and was extracted with CH2Cl2 and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was dissolved in toluene and filtered with a silica gel filter. After concentrating the filtered solution, the concentrate was recrystallized with toluene and acetone to obtain G-137 (16.24 g, 81%) of the product.
  • Synthesis of Compound G-168
  • Figure US20220278285A1-20220901-C00315
  • Sub a-117 (10 g, 22.4 mmol), Sub b-26 (11.20 g, 22.4 mmol), Pd2(dba)3 (0.62 g, 0.7 mmol), P(t-Bu)3 (0.36 g, 1.8 mmol), NaO(t-Bu) (6.47 g, 67.3 mmol) and toluene (230 mL) were placed in a round bottom flask and then the mixture was heated under reflux at 110° C. for 3 hours. When the reaction is completed, the resultant was diluted with distilled water at room temperature and was extracted with CH2Cl2 and water. Thereafter, the organic layer was dried with MgSO4 and concentrated. The concentrate was dissolved in toluene and filtered with a silica gel filter. After concentrating the filtered solution, the concentrate was recrystallized with toluene and acetone to obtain G-168 (16.92 g, 83%) of the product.
  • The FD-MS values of the compounds according to Formula A of the present invention prepared according to the above synthesis examples are shown in the following Table 7.
  • TABLE 7
    Compound FD-MS Compound FD-MS
    G-1 m/z = 652.29 (C49H36N2 = 652.84) G-2 m/z = 728.32 (C55H40N2 = 728.94)
    G-3 m/z = 804.35 (C61H44N2 = 805.04) G-4 m/z = 880.38 (C67H48N2 = 881.14)
    G-5 m/z = 880.38 (C67H48N2 = 881.14) G-6 m/z = 702.30 (C53H38N2 = 702.90)
    G-7 m/z = 778.33 (C59H42N2 = 779.00) G-8 m/z = 768.35 (C58H44N2 = 769.00)
    G-9 m/z = 844.38 (C64H48N2 = 845.10) G-10 m/z = 844.38 (C64H48N2 = 845.10)
    G-11 m/z = 884.41 (C67H52N2 = 885.17) G-12 m/z = 844.38 (C64H48N2 = 845.10)
    G-13 m/z = 844.38 (C64H48N2 = 845.10) G-14 m/z = 884.41 (C67H52N2 = 885.17)
    G-15 m/z = 968.41 (C74H52N2 = 969.24) G-16 m/z = 1008.44 (C77H56N2 = 1009.31)
    G-17 m/z = 892.38 (C68H48N2 = 893.15) G-18 m/z = 968.41 (C74H52N2 = 969.24)
    G-19 m/z = 1044.44 (C80H56N2 = 1045.34) G-20 m/z = 892.38 (C68H48N2 = 893.15)
    G-21 m/z = 966.40 (C74H50N2 = 967.23) G-22 m/z = 968.41 (C74H52N2 = 969.24)
    G-23 m/z = 1044.44 (C80H56N2 = 1045.34) G-24 m/z = 1008.44 (C77H56N2 = 1009.31)
    G-25 m/z = 968.41 (C74H52N2 = 969.24) G-26 m/z = 742.30 (C55H38N2O = 742.92)
    G-27 m/z = 823.36 (C61H37D5N2O = 824.05) G-28 m/z = 818.33 (C61H42N2O = 819.02)
    G-29 m/z = 858.36 (C64H46N2O = 859.09) G-30 m/z = 982.39 (C74H50N2O = 983.23)
    G-31 m/z = 742.30 (C55H38N2O = 742.92) G-32 m/z = 792.31 (C59H40N2O = 792.98)
    G-33 m/z = 982.39 (C74H50N2O = 983.23) G-34 m/z = 818.33 (C61H42N2O = 819.02)
    G-35 m/z = 818.33 (C61H42N2O = 819.02) G-36 m/z = 868.35 (C65H44N2O = 869.08)
    G-37 m/z = 858.36 (C64H46N2O = 859.09) G-38 m/z = 742.30 (C55H38N2O = 742.92)
    G-39 m/z = 934.39 (C70H50N2O = 935.18) G-40 m/z = 834.31 (C61H42N2S = 835.08)
    G-41 m/z = 950.37 (C70H50N2S = 951.24) G-42 m/z = 834.31 (C61H42N2S = 835.08)
    G-43 m/z = 808.29 (C59H40N2S = 809.04) G-44 m/z = 874.34 (C64H46N2S = 875.15)
    G-45 m/z = 758.28 (C55H38N2S = 758.98) G-46 m/z = 998.37 (C74H50N2S = 999.29)
    G-47 m/z = 880.38 (C67H48N2 = 881.14) G-48 m/z = 804.35 (C61H44N2 = 805.04)
    G-49 m/z = 804.35 (C61H44N2 = 805.04) G-50 m/z = 880.38 (C67H48N2 = 881.14)
    G-51 m/z = 854.37 (C65H46N2 = 855.10) G-52 m/z = 844.38 (C64H48N2 = 845.10)
    G-53 m/z = 996.44 (C76H56N2 = 997.30) G-54 m/z = 920.41 (C70H52N2 = 921.20)
    G-55 m/z = 844.38 (C64H48N2 = 845.10) G-56 m/z = 920.41 (C70H52N2 = 921.20)
    G-57 m/z = 1010.46 (C77H58N2 = 1011.33) G-58 m/z = 1044.44 (C80H56N2 = 1045.34)
    G-59 m/z = 1208.51 (C93H64N2 = 1209.55) G-60 m/z = 1118.46 (C86H58N2 = 1119.42)
    G-61 m/z = 968.41 (C74H52N2 = 969.24) G-62 m/z = 1120.48 (C86H60N2 = 1121.44)
    G-63 m/z = 868.35 (C65H44N2O = 869.08) G-64 m/z = 1058.42 (C80H54N2O = 1059.33)
    G-65 m/z = 818.33 (C61H42N2O = 819.02) G-66 m/z = 934.39 (C70H50N2O = 935.18)
    G-67 m/z = 894.36 (C67H46N2O = 895.12) G-68 m/z = 894.36 (C67H46N2O = 895.12)
    G-69 m/z = 884.32 (C65H44N2S = 885.14) G-70 m/z = 950.37 (C70H50N2S = 951.24)
    G-71 m/z = 910.34 (C67H46N2S = 911.18) G-72 m/z = 960.35 (C71H48N2S = 961.24)
    G-73 m/z = 1074.40 (C80H54N2S = 1075.39) G-74 m/z = 652.29 (C49H36N2 = 652.84)
    G-75 m/z = 880.38 (C67H48N2 = 881.14) G-76 m/z = 880.38 (C67H48N2 = 881.14)
    G-77 m/z = 844.38 (C64H48N2 = 845. 10) G-78 m/z = 920.41 (C70H52N2 = 921.20)
    G-79 m/z = 920.41 (C70H52N2 = 921.20) G-80 m/z = 960.44 (C73H56N2 = 961.27)
    G-81 m/z = 1084.48 (C83H60N2 = 1085.41) G-82 m/z = 1018.43 (C78H54N2 = 1019.30)
    G-83 m/z = 1044.44 (C80H56N2 = 1045.34) G-84 m/z = 894.36 (C67H46N2O = 895.12)
    G-85 m/z = 818.33 (C61H42N2O = 819.02) G-86 m/z = 1058.42 (C80H54N2O = 1059.33)
    G-87 m/z = 934.39 (C70H50N2O = 935.18) G-88 m/z = 844.38 (C64H48N2 = 845.10)
    G-89 m/z = 844.38 (C64H48N2 = 845.10) G-90 m/z = 920.41 (C70H52N2 = 921.20)
    G-91 m/z = 896.41 (C68H52N2 = 897.18) G-92 m/z = 1010.46 (C77H58N2 = 1011.33)
    G-93 m/z = 1036.48 (C79H60N2 = 1037.36) G-94 m/z = 884.41 (C67H52N2 = 885.17)
    G-95 m/z = 1006.43 (C77H54N2 = 1007.29) G-96 m/z = 1084.48 (C83H60N2 = 1085.41)
    G-97 m/z = 1084.48 (C83H60N2 = 1085.41) G-98 m/z = 858.36 (C64H46N2O = 859.09)
    G-99 m/z = 974.42 (C73H54N2O = 975.25) G-100 m/z = 908.38 (C68H48N2O = 909.15)
    G-101 m/z = 934.39 (C70H50N2O = 935.18) G-102 m/z = 1098.45 (C83H58N2O = 1099.39)
    G-103 m/z = 974.42 (C73H54N2O = 975.25) G-104 m/z = 874.34 (C64H46N2S = 875.15)
    G-105 m/z = 1066.43 (C79H58N2S = 1067.41) G-106 m/z = 768.35 (C58H44N2 = 769.00)
    G-107 m/z = 844.38 (C64H48N2 = 845.10) G-108 m/z = 920.41 (C70H52N2 = 921.20)
    G-109 m/z = 996.44 (C76H56N2 = 997.30) G-110 m/z = 818.37 (C62H46N2 = 819.06)
    G-111 m/z = 894.40 (C68H50N2 = 895.16) G-112 m/z = 960.44 (C73H56N2 = 961.27)
    G-113 m/z = 884.41 (C67H52N2 = 885.17) G-114 m/z = 960.44 (C73H56N2 = 961.27)
    G-115 m/z = 1058.46 (C81H58N2 = 1059.37) G-116 m/z = 1084.48 (C83H60N2 = 1085.41)
    G-117 m/z = 1160.51 (C89H64N2 = 1161.51) G-118 m/z = 1084.48 (C83H60N2 = 1085.41)
    G-119 m/z = 934.39 (C70H50N2O = 935.18) G-120 m/z = 974.42 (C73H54N2O = 975.25)
    G-121 m/z = 934.39 (C70H50N2O = 935.18) G-122 m/z =: 984.41 (C74H52N2O = 985.24)
    G-123 m/z = 990.40 (C73H54N2S = 991.31) G-124 m/z = 924.35 (C68H48N2S = 925.21)
    G-125 m/z = 874.34 (C64H46N2S = 875.15) G-126 m/z = 968.41 (C74H52N2 = 969.24)
    G-127 m/z = 1044.44 (C80H56N2 = 1045.34) G-128 m/z = 940.38 (C72H48N2 = 941.19)
    G-129 m/z = 1008.44 (C77H56N2 = 1009.31) G-130 m/z = 1084.48 (C83H60N2 = 1085.41)
    G-131 m/z = 1160.51 (C89H64N2 = 1161.51) G-132 m/z = 1132.48 (C87H60N2 = 1133.45)
    G-133 m/z = 1208.51 (C93H64N2 = 1209.55) G-134 m/z = 1208.51 (C93H64N2 = 1209.55)
    G-135 m/z = 1098.45 (C83H58N2O = 1099.39) G-136 m/z = 982.39 (C74H50N2O = 983.23)
    G-137 m/z = 1222.49 (C93H62N2O = 1223.53) G-138 m/z = 1048.39 (C78H52N2S = 1049.35)
    G-139 m/z = 892.38 (C68H48N2 = 893.15) G-140 m/z = 1044.44 (C80H56N2 = 1045.34)
    G-141 m/z = 1084.48 (C83H60N2 = 1085.41) G-142 m/z = 982.39 (C74H50N2O = 983.23)
    G-143 m/z = 1058.42 (C80H54N2O = 1059.33) G-144 m/z = 998.37 (C74H50N2S = 999.29)
    G-145 m/z = 1044.44 (C80H56N2 = 1045.34) G-146 m/z = 1120.48 (C86H60N2 = 1121.44)
    G-147 m/z = 942.40 (C72H50N2 = 943.21) G-148 m/z = 1084.48 (C83H60N2 = 1085.41)
    G-149 m/z = 1084.48 (C83H60N2 = 1085.41) G-150 m/z = 1132.48 (C87H60N2 = 1133.45)
    G-151 m/z = 1248.54 (C96H68N2 = 1249.61) G-152 m/z = 982.39 (C74H50N2O = 983.23)
    G-153 m/z = 1058.42 (C80H54N2O = 1059.33) G-154 m/z = 1112.42 (C83H56N2S = 1113.44)
    G-155 m/z = 998.37 (C74H50N2S = 999.29) G-156 m/z = 742.30 (C55H38N2O = 742.92)
    G-157 m/z = 818.33 (C61H42N2O = 819.02) G-158 m/z = 868.35 (C65H44N2O = 869.08)
    G-159 m/z = 1010.42 (C76H54N2O = 1011.28) G-160 m/z = 934.39 (C70H50N2O = 935.18)
    G-161 m/z = 984.41 (C74H52N2O = 985.24) G-162 m/z = 982.39 (C74H50N2O = 983.23)
    G-163 m/z = 1222.49 (C93H62N2O = 1223.53) G-164 m/z = 908.34 (C67H44N2O2 = 909.10)
    G-165 m/z = 1072.40 (C80H52N2O2 = 1073.31) G-166 m/z = 832.31 (C61H40N2O2 = 833.00)
    G-167 m/z = 948.37 (C70H48N2O2 = 949.17) G-168 m/z = 908.34 (C67H44N2O2 = 909.10)
    G-169 m/z = 823.36 (C61H37D5N2O = 824.05) G-170 m/z = 894.36 (C67H46N2O = 895.12)
    G-171 m/z = 970.39 (C73H50N2O = 971.22) G-172 m/z = 868.35 (C65H44N2O = 869.08)
    G-173 m/z = 858.36 (C64H46N2O = 859.09) G-174 m/z =: 934.39 (C70H50N2O = 935.18)
    G-175 m/z = 934.39 (C70H50N2O = 935.18) G-176 m/z = 1058.42 (C80H54N2O = 1059.33)
    G-177 m/z = 982.39 (C74H50N2O = 983.23) G-178 m/z = 908.34 (C67H44N2O2 = 909.10)
    G-179 m/z = 1072.40 (C80H52N2O2 = 1073.31) G-180 m/z = 908.34 (C67H44N2O2 = 909.10)
    G-181 m/z = 818.33 (C61H42N2O = 819.02) G-182 m/z = 970.39 (C73H50N2O = 971.22)
    G-183 m/z = 858.36 (C64H46N2O = 859.09) G-184 m/7 = 1058.42 (C80H54N2O = 1059.33)
    G-185 m/z = 982.39 (C74H50N2O = 983.23) G-186 m/z = 882.32 (C65H42N2O2 = 883.06)
    G-187 m/z = 908.34 (C67H44N2O2 = 909.10) G-188 m/z = 970.39 (C73H50N2O = 971.22)
    G-189 m/z = 1020.41 (C77H52N2O = 1021.28) G-190 m/z = 1010.42 (C76H54N2O = 1011.28)
    G-191 m/z = 974.42 (C73H54N2O = 975.25) G-192 m/z = 982.39 (C74H50N2O = 983.23)
    G-193 m/z = 1134.45 (C86H58N2O = 1135.42) G-194 m/z = 982.39 (C74H50N2O = 983.23)
    G-195 m/z = 908.34 (C67H44N2O2 = 909.10) G-196 m/z = 948.37 (C70H48N2O2 = 949.17)
    G-197 m/z = 924.32 (C67H44N2OS = 925.16) G-198 m/z = 802.33 (C61H42N2 = 803.02)
    G-199 m/z = 752.32 (CS7H40N2 = 752.96) G-200 m/z = 892.38 (C68H48N2 = 893.15)
    G-204 m/z = 934.39 (C70H50N2O = 935.18)
  • Fabrication and Evaluation of Organic Electric element
    • [Example 1] Green OLED (a Phosphorescent Host)
  • N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (hereinafter, “2-TNATA”) was vacuum-deposited on the ITO layer formed on a glass substrate to form a hole injection layer with a thickness of nm.
  • Next, 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, “NPD”) was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 60 nm.
  • Subsequently, a light emitting layer with a thickness of 30 nm was vacuum-deposited on the hole transport layer by using compound 1-1 of the present invention as a host material and tris(2-phenylpyridine)-iridium (hereinafter, “Ir(ppy)3”) as a dopant material in a weight ratio of 95:5.
  • Subsequently, (1,1′-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter, “BAlq”) was vacuum-deposited with a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and tris-(8-hydroxyquinoline)aluminum (hereinafter, “Alq3”) was vacuum-deposited with a thickness of 40 nm on the hole blocking layer to form an electron transport layer.
  • Next, LiF was deposited with a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then Al was deposited with a thickness of nm on the electron injection layer to form a cathode.
    • [Example 2] to [Example 15]
  • The OLED was fabricated in the same manner as described in Example 1 except that compounds of the present invention described in Table 5 instead of the compound 1-1 of the present invention was used as host material of a light emitting layer.
    • [Comparative Example 1] to [Comparative Example 3]
  • The OLEDs were fabricated in the same manner as described in Example 1 except that one of the comparative compounds 1 to 3 instead of compound 1-1 of the present invention was used as host material of a light emitting layer.
  • Figure US20220278285A1-20220901-C00316
  • Electroluminescence (EL) characteristics were measured with PR-650 (Photoresearch) by applying a forward bias DC voltage to the OLEDs prepared in Examples 1 to 15 of the present invention and Comparative Examples 1 to 3. And, the T95 life time was measured using a life time measuring apparatus manufactured by Mcscience Inc. at reference brightness of 5000 cd/m2. The measurement results are shown in Tables 8 below.
  • TABLE 8
    Current
    Voltage Density Brightness Efficiency Lifetime CIE
    Compound (V) (mA/cm2) (cd/m2) (cd/A) T(95) x y
    comp.Ex(1) comp.Com 1 5.9 21.2 5000 23.6 56.1 0.33 0.61
    comp.Ex(2) comp.Com 2 5.8 15.9 5000 31.5 75.4 0.33 0.61
    comp.Ex(3) comp.Com 3 5.8 15.1 5000 33.2 77.1 0.33 0.61
    Ex.(1) Com. 1-1 5.7 13.8 5000 36.2 84.3 0.33 0.62
    Ex.(2) Com. 1-2 5.6 14.1 5000 35.4 85.1 0.33 0.61
    Ex.(3) Com. 1-98 5.6 13.7 5000 36.4 84.8 0.33 0.62
    Ex.(4) Com. 1-100 5.7 14.2 5000 35.2 82.1 0.33 0.62
    Ex.(5) Com. 2-1 5.6 13.3 5000 37.6 85.6 0.33 0.61
    Ex.(6) Com. 2-3 5.5 13.4 5000 37.2 86.6 0.33 0.61
    Ex.(7) Com. 2-15 5.5 12.9 5000 38.9 87.5 0.33 0.62
    Ex.(8) Com. 2-35 5.5 13.3 5000 37.7 87.2 0.33 0.62
    Ex.(9) Com. 3-6 5.5 13.7 5000 36.5 85.9 0.33 0.61
    Ex.(10) Com. 4-33 5.7 14.2 5000 35.1 80.7 0.33 0.62
    Ex.(11) Com. 4-37 5.5 13.1 5000 38.2 87.8 0.33 0.61
    Ex.(12) Com. 4-39 5.7 14.2 5000 35.3 81.5 0.33 0.61
    Ex.(13) Com. 4-42 5.7 14.2 5000 35.2 81.0 0.33 0.61
    Ex.(14) Com. 4-43 5.7 14.2 5000 35.1 81.2 0.33 0.61
    Ex.(15) Com. 4-45 5.7 14.1 5000 35.4 80.9 0.33 0.61
    • [Example 16] to [Example 55]
  • The OLED was fabricated in the same manner as described in Example 1 except that a mixture of the compound represented by Formula 1 and the compound represented by Formula 12 of the present invention described in Table 6 instead of compound 1-1 of the present invention was used as host material of a light emitting layer.
    • [Comparative Example 4] and [Comparative Example 6]
  • The OLEDs were fabricated in the same manner as described in Example 1 except that a mixture of comparative compound 2 and compound 5-27 of the present invention (Comparative Example 4), or a mixture of comparative compound 3 and compound 5-27 of the present invention instead of compound 1-1 of the present invention was used as host material of a light emitting layer.
  • Electroluminescence (EL) characteristics were measured with PR-650 (Photoresearch) by applying a forward bias DC voltage to the OLEDs prepared in Examples 16 to 55 of the present invention and Comparative Examples 4 and 5. And, the T95 life time was measured using a life time measuring apparatus manufactured by Mcscience Inc. at reference brightness of 5000 cd/m2. The measurement results are shown in Tables 9 below.
  • TABLE 9
    Current
    Voltage Density Brightness Efficiency Lifetime
    Host 1 Host 2 (V) (mA/cm2) (cd/m2) (cd/A) T(95)
    comp.Ex(4) comp.Com 2 Com. 5-27 5.6 14.8 5000 33.8  83.7
    comp.Ex(5) comp.Com 3 Com. 5-27 5.6 14.0 5000 35.7  86.3
    Ex.(16) Com. 1-1 Com. 5-27 5.0 11.9 5000 42.1 105.3
    Ex.(17) Com. 1-2 5.0 11.9 5000 41.9 106.4
    Ex.(18) Com. 1-98 5.0 11.9 5000 42.0 106.0
    Ex.(19) Com. 1-100 5.1 12.0 5000 41.8 105.1
    Ex.(20) Com. 2-3 5.0 11.8 5000 42.4 106.9
    Ex.(21) Com. 2-15 5.0 11.7 5000 42.9 107.0
    Ex.(22) Com. 2-35 5.0 11.7 5000 42.6 106.7
    Ex.(23) Com. 3-6 5.0 11.9 5000 42.0 106.5
    Ex.(24) Com. 4-33 5.1 12.0 5000 41.8 104.9
    Ex.(25) Com. 4-37 5.0 11.7 5000 42.7 107.2
    Ex.(26) Com. 1-1 Com. 5-25 5.1 12.3 5000 40.6 103.2
    Ex.(27) Com. 1-2 5.1 12.3 5000 40.7 103.9
    Ex.(28) Com. 1-98 5.1 12.1 5000 41.2 103.5
    Ex.(29) Com. 1-100 5.2 12.2 5000 40.9 102.8
    Ex.(30) Com. 2-3 5.1 12.0 5000 41.5 104.6
    Ex.(31) Com. 2-15 5.1 12.0 5000 41.7 104.7
    Ex.(32) Com. 2-35 5.1 12.1 5000 41.2 104.2
    Ex.(33) Com. 3-6 5.1 12.2 5000 41.1 104.0
    Ex.(34) Com. 4-33 5.2 12.3 5000 40.6 102.5
    Ex.(35) Com. 4-37 5.1 12.0 5000 41.6 104.8
    Ex.(36) Com. 1-1 Com. 5-31 4.9 11.5 5000 43.6 107.7
    Ex.(37) Com. 1-2 4.9 11.5 5000 43.3 108.2
    Ex.(38) Com. 1-98 4.9 11.5 5000 43.5 107.9
    Ex.(39) Com. 1-100 5.0 11.6 5000 43.1 107.2
    Ex.(40) Com. 2-3 4.9 11.4 5000 43.9 109.0
    Ex.(41) Com. 2-15 4.9 11.3 5000 44.2 109.2
    Ex.(42) Com. 2-35 4.9 11.4 5000 44.0 108.8
    Ex.(43) Com. 3-6 4.9 11.4 5000 43.8 108.5
    Ex.(44) Com. 4-33 5.0 11.6 5000 43.0 107.1
    Ex.(45) Com. 4-37 4.9 11.4 5000 44.0 109.3
    Ex.(46) Com. 1-1 Com. 5-42 5.2 12.7 5000 39.5 101.0
    Ex.(47) Com. 1-2 5.2 12.5 5000 40.0 101.5
    Ex.(48) Com. 1-98 5.2 12.5 5000 39.9 101.2
    Ex.(49) Com. 1-100 5.2 12.7 5000 39.4 100.7
    Ex.(50) Com. 2-3 5.2 12.6 5000 39.7 102.1
    Ex.(51) Com. 2-15 5.2 12.4 5000 40.3 102.4
    Ex.(52) Com. 2-35 5.2 12.5 5000 40.1 102.0
    Ex.(53) Com. 3-6 5.2 12.6 5000 39.6 101.7
    Ex.(54) Com. 4-33 5.2 12.7 5000 39.4 100.5
    Ex.(55) Com. 4-37 5.2 12.5 5000 40.0 102.4
    • Example 56
  • After 2-TNATA was vacuum-deposited on the ITO layer formed on a glass substrate to form a hole injection layer with a thickness of 60 nm, NPD was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 60 nm.
  • Next, compound 14-69 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form an emission-auxiliary layer, and a light emitting layer with a thickness of 30 nm was vacuum-deposited on the hole transport layer by using a mixture of compound 1-1(the first host) and compound 5-27 (the second host) of the present invention in the ratio of 6:4 as a host material and Ir(ppy)3) as a dopant material in a weight ratio of 95:5.
  • Subsequently, BAlq was vacuum-deposited with a thickness of 10 nm on the light emitting layer to form a hole blocking layer, Alq3 was vacuum-deposited with a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Next, LiF was deposited with a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then Al was deposited with a thickness of 150 nm on the electron injection layer to form a cathode.
    • [Example 57] to [Example 73]
  • The OLEDs were fabricated in the same manner as described in Example 56 except that the compounds of the present invention described in the following Table 7 were used as an emission-auxiliary layer material and the first host material.
    • [Comparative Example 6] and [Comparative Example 7]
  • The OLEDs were fabricated in the same manner as described in Example 56 except that Comparative compound 2 or 3 was used as the first host material.
  • Electroluminescence (EL) characteristics were measured with a PR-650 (Photoresearch) by applying a forward bias DC voltage to the OLEDs prepared in Examples 56 to 73 of the present invention and Comparative Examples 6 and 7. And, the T95 life time was measured using a life time measuring apparatus manufactured by Mcscience Inc. at reference brightness of 5000 cd/m2. The measurement results are shown in Tables 10 below.
  • TABLE 10
    Current
    Voltage Density Brightness Efficiency Lifetime
    EAL Host 1 Host 2 (V) (mA/cm2) (cd/m2) (cd/A) T(95)
    comp.Ex(6) 14-69 comp.Com 2 5-27 5.4 13.6  5000 36.8  88.4
    comp.Ex(7) comp.Com 3 5.4 13.1  5000 38.1  91.5
    Ex.(56) Com. 1-1 5.1 9.8 5000 51.0 123.5
    Ex.(57) Com. 1-2 5.1 9.3 5000 53.6 125.6
    Ex.(58) Com. 1-98 5.1 9.5 5000 52.6 124.4
    Ex.(59) Com. 2-3 5.0 9.2 5000 54.1 127.4
    Ex.(60) Com. 2-15 4.9 9.1 5000 54.7 128.0
    Ex.(61) Com. 4-37 4.9 9.2 5000 54.5 128.2
    comp.Ex(8) 14-72 comp.Com 2 5.4 12.6  5000 39.6  92.6
    comp.Ex(9) comp.Com 3 5.3 12.0  5000 41.6  95.1
    Ex.(62) Com. 1-1 4.9 9.0 5000 55.8 128.8
    Ex.(63) Com. 1-2 4.9 8.8 5000 56.7 130.2
    Ex.(64) Com. 1-98 4.9 8.9 5000 56.4 129.7
    Ex.(65) Com. 2-3 4.8 8.4 5000 59.7 131.6
    Ex.(66) Com. 2-15 4.8 8.3 5000 60.5 133.8
    Ex.(67) Com. 4-37 4.8 8.3 5000 60.1 134.0
    comp.Ex(10) 14-74 comp.Com 2 5.3 11.6  5000 43.1  96.7
    comp.Ex(11) comp.Com 3 5.3 10.8  5000 46.3  99.2
    Ex.(68) Com. 1-1 4.8 8.1 5000 61.7 134.2
    Ex.(69) Com. 1-2 4.8 8.0 5000 62.4 137.6
    Ex.(70) Com. 1-98 4.8 8.1 5000 62.0 135.2
    Ex.(71) Com. 2-3 4.7 7.9 5000 63.2 138.1
    Ex.(72) Com. 2-15 4.7 7.8 5000 64.1 138.8
    Ex.(73) Com. 4-37 4.7 7.8 5000 63.9 139.6
    • Example 74
  • After 2-TNATA was vacuum-deposited on the ITO layer formed on a glass substrate to form a hole injection layer with a thickness of 60 nm, the compound 14-69 of the present invention was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 60 nm. Next, the compound 14-72 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form an emission-auxiliary layer and a light emitting layer with a thickness of 30 nm was vacuum-deposited on the hole transport layer by using a mixture of the compound 1-1(the first host) and the compound 5-27(the second host) of the present invention at 6:4 as a host material and Ir(ppy)3) as a dopant material in a weight ratio of 95:5.
  • Subsequently, BAlq was vacuum-deposited with a thickness of 10 nm on the light emitting layer to form a hole blocking layer, Alq3 was vacuum-deposited with a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Next, LiF was deposited with a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then Al was deposited with a thickness of 150 nm on the electron injection layer to form a cathode.
    • [Example 75] to [Example 85]
  • The OLEDs were fabricated in the same manner as described in Example 74 except that the compounds of the present invention described in the following Table 8 were used as an emission-auxiliary layer material and the first host material.
  • Electroluminescence (EL) characteristics were measured with a PR-650 (Photoresearch) by applying a forward bias DC voltage to the OLEDs prepared in Examples 74 to 85 of the present invention. And, the T95 life time was measured using a life time measuring apparatus manufactured by Mcscience Inc. at reference brightness of 5000 cd/m2. The measurement results are shown in Tables 11 below.
  • TABLE 11
    Current
    Voltage Density Brightness Efficiency Lifetime
    HTL EAL Host 1 Host 2 (V) (mA/cm2) (cd/m2) (cd/A) T(95)
    Ex.(74) 14-69 14-72 Com. 1-1 5-27 4.6 7.9 5000 63.2 135.2
    Ex.(75) Com. 1-2 4.5 7.6 5000 65.6 138.4
    Ex.(76) Com. 1-98 4.5 7.7 5000 65.2 137.1
    Ex.(77) Com. 2-3 4.4 7.4 5000 67.6 139.4
    Ex.(78) Com. 2-15 4.4 7.3 5000 68.2 140.0
    Ex.(79) Com. 4-37 4.3 7.4 5000 68.0 140.6
    Ex.(80) 14-74 Com. 1-1 4.5 7.7 5000 65.3 141.2
    Ex.(81) Com. 1-2 4.4 7.4 5000 67.8 145.2
    Ex.(82) Com. 1-98 4.4 7.5 5000 67.1 144.0
    Ex.(83) Com. 2-3 4.3 7.3 5000 68.4 146.4
    Ex.(84) Com. 2-15 4.3 7.2 5000 69.0 147.0
    Ex.(85) Com. 4-37 4.2 7.3 5000 68.7 147.3
  • From Tables 5 to 8, it can be seen that the driving voltage of the organic electroluminescent device can be lowered and the luminous efficiency and lifespan are significantly improved when the material for an organic electroluminescent device of the present invention is used as a phosphorescent host material.
  • In particular, referring to Table 5, it can be seen that even when the compound represented by Formula 1 of the present invention is used as a single host, device characteristics are superior to that using a comparative compound.
  • These results can be explained by the LUMO value of Compound 1-1 of the present invention. Referring to Table 9A below, it can be seen that the LUMO level of Comparative Compound 2 is the highest, the LUMO level of Comparative Compound is the lowest, and the LUMO level of Compound 1-1 of the present invention is located in the middle.
  • TABLE 9A
    comp. Com2 comp. Com3 Com. 1-1
    LUMO 1.939 1.839 1.877
  • When comparing Comparative Compounds 2 and 3, Comparative Compound 2 is different in that the heteroatom of both heterocycles attached to the triazine is S, while in case of Comparative Compound 3, the heteroatom is O. From Table 9 above, it can be seen that when heteroatoms S are introduced into both heterocycles, the LUMO value is highest (comparative compound 2), and when O is introduced, the LUMO value is lowest (comparative compound 3), the LUMO value is located in the middle when S as a heteroatom is introduced into one heterocycle and O is introduced into the other heterocycle as the compound of the present invention.
  • When comparative compound 2 having the highest LUMO level is used as the phosphorescent host material, the LUMO level is too high, and thus the LUMO level acts as a barrier to electron movement. Therefore, the electron transfer from the electron transport layer to the light emitting layer is not easy, and the charge balance in the light emitting layer is reduced.
  • In addition, when comparative compound 3 having the lowest LUMO level is used as a phosphorescent host material, the energy gap between the electron transport layer and the LUMO level becomes too large, so that electrons cannot be smoothly transferred from the electron transport layer to the light emitting layer, as a result, the charge balance within the light emitting layer is reduced.
  • On the other hand, when the compound of the present invention in which the LUMO level is located in the middle of the LUMO level of the comparative compounds is used as a phosphorescent host material, it has an appropriate LUMO level for electron transfer, so the biased electron transfer characteristics of Comparative Compound 2 and Comparative Compound 3 can be complemented. Therefore, when the compound of the present invention is used as a phosphorescent host material, the charge balance in the light-emitting layer increases, so that the luminous efficiency and lifetime of the organic electroluminescent device are improved.
  • In Table 9A, compound 1-1 of the present invention is used as an example, but the same conclusion can be reached with the compounds of the present invention used in Examples 2 to 15 as a phosphorescent host material.
  • On the other hand, referring to the device results of the embodiments of the present invention, it can be seen that performance is improved in all aspects of driving voltage, efficiency, and lifetime when 1-dibenzofuran is substituted rather than 4-dibenzofuran, and when 2-position of 1-dibenzofuran is substituted rather than 4-position.
  • In more detail, it can be seen that the device result of Example 5 in which 1-dibenzofuran is substituted in triazine is better than Example 1 in which 4-dibenzofuran is substituted in triazine, and the electrical properties of the device of Example 7 in which a substituent is attached at 2-position in benzene of 1-dibenzofuran instead of 4-position are improved.
  • This suggests that the energy level of the compound (HOMO, LUMO, T1, etc.) and deposition conditions (for example, Td, etc.) are changed because the physical properties of the compound change depending on the substitution position, and this acts as a major factor (e.g. energy balance) in improving device performance, which can lead to different device results.
  • The above description can be equally applied to the case of using one compound of the present invention as a host, as well as when using two or more hosts and even when used in combination with other layers.
  • In addition, as can be seen from the device measurement results of Examples 1, 2, 5 and 6 of the present invention, it can be seen that when a substituent (Ar2, Ar3) attached to a heterocycle (dibenzofuran, dibenzothiophene) attached to a triazine is mutually asymmetric, device performance is further improved. It is believed that when Ar2 and Ar3 are mutually asymmetric, due to the non-planarity of the compound, charges are appropriately localized and the flow of the conjugate system is effectively controlled to improve the lifetime of the device.
    • [Example 86] Green OLED (an Emission-Auxiliary Layer)
  • After 2-TNATA was vacuum-deposited on the ITO(anode) layer formed on a glass substrate to form a hole injection layer with a thickness of 60 nm, NPD was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 60 nm. Next, compound G-1 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form an emission-auxiliary layer and a light emitting layer with a thickness of 30 nm was vacuum-deposited on the hole transport layer by using 4,4′-N,N′-dicarbazole-biphenyl (hereinafter, “CBP”) and Ir(ppy)3) as a dopant material in a weight ratio of 95:5. Subsequently, BAlq was vacuum-deposited with a thickness of 10 nm on the light emitting layer to form a hole blocking layer, Alq3 was vacuum-deposited with a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Next, LiF was deposited with a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then Al was deposited with a thickness of 150 nm on the electron injection layer to form a cathode.
    • [Example 87] to [Example 116]
  • The OLEDs were fabricated in the same manner as described in Example 86 except that the compounds of the present invention described in the following Table 12, instead of compound G-1 of the present invention, were used as an emission-auxiliary layer material.
    • Comparative Example 12
  • The OLED was fabricated in the same manner as described in Example 86 except that an emission-auxiliary layer was not formed.
    • [Comparative Example 13] to [Comparative Example 16]
  • The OLEDs were fabricated in the same manner as described in Example 86 except that the following Comparative compounds ref 1 to ref 4, respectively, instead of compound P-1 of the present invention, were used as an emission-auxiliary layer material.
  • Figure US20220278285A1-20220901-C00317
  • Electroluminescence (EL) characteristics were measured with PR-650 (Photoresearch) by applying a forward bias DC voltage to the OLEDs prepared in Examples 86 to 116 of the present invention and Comparative Examples 12 to 16. And, the T95 life time was measured using a life time measuring apparatus manufactured by Mcscience Inc. at reference brightness of 5000 cd/m2. The measurement results are shown in Tables 12 below.
  • TABLE 12
    Current
    Voltage Density Brightness Efficiency Lifetime CIE
    Compound (V) (mA/cm2) (cd/m2) (cd/A) T(95) x y
    comp.Ex(12) — 5.9 13.6  5000 36.8 116.9 0.33 0.61
    comp.Ex(13) ref 1 5.8 12.9  5000 38.9 119.2 0.33 0.61
    comp.Ex(14) ref 2 5.6 11.3  5000 44.2 121.3 0.33 0.61
    comp.Ex(15) ref 3 5.5 9.8 5000 50.8 125.4 0.33 0.60
    comp.Ex(16) ref 4 5.7 11.4  5000 43.9 121.8 0.33 0.61
    Ex.(86) Com. G-1 4.8 7.0 5000 71.9 143.0 0.33 0.63
    Ex.(87) Com. G-9 4.9 7.3 5000 68.5 139.7 0.33 0.62
    Ex.(88) Com. G-14 4.8 6.9 5000 72.3 143.4 0.33 0.63
    Ex.(89) Com. G-15 5.0 7.4 5000 67.5 137.8 0.33 0.63
    Ex.(90) Com. G-27 4.6 6.6 5000 75.3 144.7 0.33 0.62
    Ex.(91) Com. G-29 4.5 6.6 5000 76.3 145.5 0.33 0.63
    EL(92) Com. G-39 4.9 7.2 5000 69.8 141.9 0.33 0.63
    EL(93) Com. G-42 4.6 6.6 5000 75.6 144.5 0.33 0.63
    Ex.(94) Com. G-47 5.1 7.5 5000 67.0 137.5 0.33 0.63
    Ex.(95) Com. G-50 4.8 7.0 5000 71.1 142.8 0.33 0.63
    Ex.(96) Com. G-51 4.9 7.4 5000 67.7 138.3 0.33 0.62
    EL(97) Com. G-52 4.5 6.7 5000 74.9 144.9 0.33 0.62
    EL(98) Com. G-55 4.9 7.3 5000 68.4 139.5 0.33 0.62
    EL(99) Com. G-58 5.2 7.6 5000 65.8 136.8 0.33 0.63
    Ex.(100) Com. G-66 4.5 6.6 5000 76.0 145.1 0.33 0.63
    Ex.(101) Com. G-71 5.2 7.7 5000 65.1 135.3 0.33 0.62
    Ex.(102) Com. G-74 4.9 7.3 5000 68.8 141.2 0.33 0.62
    Ex.(103) Com. G-82 5.1 7.5 5000 66.4 137.3 0.33 0.63
    Ex.(104) Com. G-99 5.2 7.6 5000 66.1 135.6 0.33 0.63
    Ex.(105) Com. G-101 4.9 7.2 5000 69.3 141.6 0.33 0.63
    Ex.(106) Com. G-115 5.2 7.7 5000 64.9 137.0 0.33 0.62
    Ex.(107) Com. G-176 5.2 7.7 5000 65.3 135.0 0.33 0.63
    Ex.(108) Com. G-190 5.0 7.4 5000 68.0 138.6 0.33 0.63
    Ex.(109) Com. G-193 5.2 7.7 5000 65.0 136.0 0.33 0.63
    Ex.(110) Com. G-198 4.8 7.1 5000 70.7 142.4 0.33 0.63
    Ex.(111) Com. G-199 4.8 7.1 5000 70.3 142.1 0.33 0.62
    Ex.(112) Com. G-200 4.9 7.3 5000 68.2 139.0 0.33 0.63
    Ex.(113) Com. G-201 4.7 6.7 5000 74.3 144.3 0.33 0.62
    Ex.(114) Com. G-202 4.7 6.8 5000 73.8 144.1 0.33 0.62
    Ex.(115) Com. G-203 4.7 6.8 5000 73.1 143.8 0.33 0.62
    Ex.(116) Com. G-204 4.7 6.9 5000 72.6 143.6 0.33 0.63
  • As can be seen from the results of Table 12, when a green organic electroluminescent device was manufactured by using the compounds of the present invention as material for an emission-auxiliary layer, the driving voltage of the organic electroluminescent device is lowered, and luminous efficiency and lifetime can be improved, compared to the comparative examples not forming an emission-auxiliary layer, or using Ref 1 to Ref 4 as material of an emission-auxiliary layer. That is, in the case of Comparative Examples 13 to 16 in which the emission-auxiliary layer was formed using one of the comparative compounds ref 1 to ref 4 rather than Comparative Example 12 in which an emission-auxiliary layer was not formed, the driving voltage, efficiency, and lifetime of the device were improved.
  • Ref 1, Ref 3 and Ref 4 differ in the substituents connected to the nitrogen atom of the amine group in the NPB type. A phenyl derivative (biphenyl) is attached to the nitrogen atom of the amine group in Ref 1, while diphenyl fluorene is attached to the nitrogen atom in Ref 3 and Ref 4. Looking at the device characteristics of Comparative Example 13, 15, and 16 using these compounds as material of an emission-auxiliary layer, it can be seen that the device characteristics of Comparative Example 15 and are superior to those of Comparative Example 13.
  • In addition, comparing Ref 2 and Ref 4, Ref 4 contains one additional amine group and carbazole is bound to the additional amine group, compared to Ref 2. Looking at the device characteristics of Comparative Example 14 and 16 using these compounds as material of an emission-auxiliary layer, it can be seen that efficiency and lifetime are similar, but the driving voltage is better in Comparative Example 14.
  • From these results, it can be seen that even if compounds having similar structures are used for devices, the characteristics of the devices may vary depending on the substitution position of the substituent and the type of the substituent. This seems to be due to differences in the properties of the compounds when they have different types of substituents and the position substituted, and due to these differences, the physical properties of the compound act as a major factor in improving device performance (e.g., energy balance) when depositing the compound in the device manufacturing process.
  • Comparing the compound of the present invention and Ref 3, it is the same in that the two amine groups are bonded through an arylene linking group, and diphenylfluorene is bonded to the nitrogen atom of the amine group, but there is a difference in that the position where the nitrogen of the amine group is bonded is reverse phenyl(i.e., refers to the phenyl of the diphenyl position rather than the fluorene backbone of the 9,9-diphenyl-fluorene structure) in case of the present invention, while the position is the backbone benzene in case of Ref 3. Due to this difference, it can be seen that the driving voltage, lifetime, and efficiency are significantly improved when the compound of the present invention is used as material of an emission-auxiliary layer, compared to Comparative Example 15 using Ref 3.
  • It appears that this is because the physical properties of the compound including LUMO, HOMO, band gap and T1 value are changed depending on where the amine group is attached to the diphenylfluorene and this difference in physical properties serves as a major factor influencing device characteristics when depositing a compound for forming an emission-auxiliary layer in a device manufacturing process.
  • In addition, comparing the device results of Examples 86, 90, 91, and 97 of the present invention, it can be seen that the driving voltage, efficiency, and lifetime of the device when a specific substituent other than a simple aryl group is substituted with a substituent of an amine group. That is, the device results of Examples 90 and 97 showed better values than Example 86, wherein a compound (G-27 or G-52) substituted with dibenzofuran or fluorene containing a hetero atom is used in Examples 90 and 97 and Compound G-1 in which a simple phenyl group was substituted with a substituent of an amine group was used as material of an emission-auxiliary layer in Example 86, and the device results of Examples 91 showed better values than Examples 90 and 97, wherein a compound G-29 in which fluorene and dibenzofuran are linked to one nitrogen atom of the amine group is used in Example 91.
  • Further, comparing Examples 100 and 106 of the present invention, it can be seen that the device results of Example 100 are further improved than Example 105, wherein fluorene-substituted compound G-101 at a nitrogen atom connected to diphenylfluorene is used as material of an emission-auxiliary layer in Example 105, and compound G-66 in which fluorene is substituted at a nitrogen atom of another amine group other than the nitrogen atom connected to diphenylfluorene is used as material of an emission-auxiliary layer in Example 100.
  • In addition, comparing Examples 86 and 102 of the present invention, it can be seen that the device results of Example 86 are further improved than Example 102 when two amine groups of the compound of the present invention are linked to each other through a phenyl linker, wherein a compound G-1 in which two amine groups are linked to the linker phenyl in a meta position is used as material of an emission-auxiliary layer in Example 86 and compound G-74 in which two amine groups are para-linked to phenyl is used as material of an emission-auxiliary layer in Example 102.
  • It appears that this is because when the structure of the compound is changed according to the type of substituent, the position of substitution and the method of substitution, the physical properties of the compound are changed, and as a result, physical properties are changed to improve the properties of the device when an emission-auxiliary layer is formed.
  • Although exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art will appreciate that various modifications can be made without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in the present invention are intended to illustrate the present invention, and the scope of the present invention is not limited by the embodiments. The scope of the present invention shall be construed on the basis of the accompanying claims, and it shall be construed that all of the technical ideas included within the scope equivalent to the claims belong to the present invention.

Claims (13)

1. A compound of Formula 24:
Figure US20220278285A1-20220901-C00318
wherein Ar4, Ar5, Ar10 and Ar11 are each independently a C6-C20 aryl group or a fluorenyl group,
L5 is a C12-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O and S,
wherein Ar4, Ar5, Ar10, Ar11 and L5 may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, a C1-C20 alkyl group, a C6-C20 aryl group, and a C6-C20 aryl group substituted with deuterium.
2. The compound of claim 1, wherein L5 is a dibenzofuran or dibenzothiophene group.
3. The compound of claim 1, wherein Ar4 and Ar5 are each independently a C6-C12 aryl group, and Ar10 and Ar11 are each independently a C6-C12 aryl group or a fluorenyl group.
4. The compound of claim 1, wherein Ar4 and Ar5 are each independently a phenyl or biphenyl group, and one of Ar10 and Ar11 is a phenyl or biphenyl group and the other is a 9,9-dimethyl-9H-fluorenyl group.
5. The compound of claim 4, wherein Ar4 and Ar5 are each independently a phenyl group, Ar10 is a biphenyl group, Ar11 is a 9,9-dimethyl-9H-fluorenyl group.
6. The compound of claim 1, wherein either Ar10 or Ar11 is a 2-(9,9-dimethyl-9H)-fluorenyl or 2-(9,9-diphenyl-9H)-fluorenyl group.
7. The compound of claim 1, wherein the compound of Formula 24 is Compound 15-7 or Compound 15-8:
Figure US20220278285A1-20220901-C00319
8. An organic electric element comprising a first electrode, a second electrode and an organic material layer formed between the first and the second electrodes, wherein the organic material layer comprises the compound of Formula 24 of claim 1.
9. The organic electric element of claim 8, wherein the organic material layer comprises a light emitting layer, and an emission-auxiliary layer formed between the light emitting layer and the first electrode, wherein the emission-auxiliary layer comprises the compound of Formula 24.
10. The organic electric element of claim 9, wherein the organic material layer further comprises a hole transport layer formed between the light emitting layer and the first electrode, and the hole transport layer comprises a compound of Formula 21 or 22:
Figure US20220278285A1-20220901-C00320
wherein:
Ar4, Ar5 and Ar9 are each independently selected from the group consisting of a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, C3-C20 aliphatic ring, and a fused ring group formed by a C3-C20 aliphatic ring with a C6-C20 aromatic ring, of a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxyl group, a C6-C20 aryloxy group and -L′-N(Ra)(Rb),
L5 is selected from the group consisting of a C6-C20 arylene group, a fluorenylene group, and a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 aliphatic ring and a fused ring group formed by a C3-C20 aliphatic ring with a C6-C20 aromatic ring,
L6 is selected from the group consisting of a single bond, a C6-C20 arylene group, a fluorenylene group, and a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 aliphatic ring and a fused ring group formed by a C3-C20 aliphatic ring with a C6-C20 aromatic ring,
R6 to R9 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 aliphatic ring, a fused ring group formed by a C3-C20 aliphatic ring with a C6-C20 aromatic ring, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxyl group, a C6-C20 aryloxy group and -L′-N(Ra)(Rb), wherein adjacent groups may be linked to each other to form a ring,
h, i and g are each an integer of 0 to 4, j is an integer of 0 to 3, where each of these is an integer of 2 or more, a plurality of R6s, a plurality of R7s, a plurality of R8s, and a plurality of R9s are the same as or different from each other,
L′ is selected from the group consisting of a single bond, a C6-C20 arylene group, a fluorenylene group, and a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 aliphatic ring, and a fused ring group formed by a C3-C20 aliphatic ring with a C6-C20 aromatic ring,
Ra and Rb are each independently selected from the group consisting of a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 aliphatic ring and a fused ring group formed by a C3-C20 aliphatic ring with a C6-C20 aromatic ring,
wherein Ar4, Ar5, Ar9, R6 to R9, Ra, Rb, L5, L6, L′ and the ring formed by adjacent groups may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a fused ring group formed by a C3-C20 aliphatic ring with a C6-C20 aromatic ring, a C7-C20 arylalkyl group, a C8-C20 arylalkenyl group and a combination thereof.
11. The organic electric element of claim 9, wherein the light emitting layer comprises a compound of Formula 12:
Figure US20220278285A1-20220901-C00321
wherein:
Z1 to Z4, Z13 to Z16 are independently C(R) or N,
Z5 to Z12 are independently C, C(R) or N,
L2 is selected from the group consisting of a single bond, a C6-C20 arylene group, a fluorenylene group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 aliphatic ring, and a fused ring group formed by a C3-C20 aliphatic ring with a C6-C20 aromatic ring,
W is N(Ar5), N, O, S, C(R′) or C(R′)(R″), and W is N or C(R′) where W is combined with L2,
Ar4 and Ar5 are each independently selected from the group consisting of a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 aliphatic ring, a fused ring group formed by a C3-C20 aliphatic ring with a C6-C20 aromatic ring, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxyl group, a C6-C20 aryloxy group, -L′-N(Ra)(Rb) and a combination thereof,
R, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 aliphatic ring, a fused ring group formed by a C3-C20 aliphatic ring with a C6-C20 aromatic ring, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxyl group, a C6-C20 aryloxy group and -L′-N(Ra)(Rb), wherein adjacent R groups may be optionally linked to each other to form a ring, and R′ and R″ may be optionally linked to each other to form a ring,
L′ is selected from the group consisting of a single bond, a C6-C20 arylene group, a fluorenylene group, and a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 aliphatic ring, and a fused ring group formed by a C3-C20 aliphatic ring with a C6-C20 aromatic ring, and
Ra and Rb are each independently selected from the group consisting of a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 aliphatic ring, and a fused ring group formed by a C3-C20 aliphatic ring with a C6-C20 aromatic ring,
wherein L2, Ar4, Ar5, R, R′, R″, the ring formed by adjacent R, and the ring formed by R′ and R″ are each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a phosphine oxide group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a fused ring group formed by a C3-C20 aliphatic ring with a C6-C20 aromatic ring, a C7-C20 arylalkyl group, a C8-C20 arylalkenyl group and a combination thereof.
12. An electronic device comprising a display device comprising the organic electric element of claim 8, and a control unit for driving the display device.
13. The electronic device of claim 12, wherein the organic electric element is one of an organic light emitting diode, an organic solar cell, an organic photo conductor, an organic transistor, and an element for monochromatic or white illumination.
US17/346,936 2017-09-29 2021-06-14 Compound for organic electric element, organic electric element comprising the same, and electronic device thereof Pending US20220278285A1 (en)

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Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11456432B2 (en) * 2017-11-01 2022-09-27 Idemitsu Kosan Co., Ltd. Top emission organic electroluminescent element, organic electroluminescent light emitting device, and electronic device
KR102537898B1 (en) * 2018-05-28 2023-05-31 솔루스첨단소재 주식회사 Organic compound and organic electroluminescent device comprising the same
US11802124B2 (en) 2018-07-09 2023-10-31 Lg Chem, Ltd. Compound and organic light emitting diode comprising same
CN109400560A (en) * 2018-10-18 2019-03-01 长春海谱润斯科技有限公司 A kind of aromatic amine compound and its organic electroluminescence device
US11807632B2 (en) * 2018-10-22 2023-11-07 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
KR20210098447A (en) 2018-11-30 2021-08-10 이데미쓰 고산 가부시키가이샤 Compounds, materials for organic electroluminescent devices, organic electroluminescent devices, and electronic devices
KR20200127628A (en) * 2019-05-03 2020-11-11 덕산네오룩스 주식회사 An organic electronic element comprising compound for organic electronic element and an electronic device thereof
KR20200131681A (en) * 2019-05-14 2020-11-24 덕산네오룩스 주식회사 An organic electronic element comprising compound for organic electronic element and an electronic device thereof
KR102392659B1 (en) * 2019-05-22 2022-04-29 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
WO2020235955A1 (en) * 2019-05-22 2020-11-26 주식회사 엘지화학 Novel compound and organic light-emitting device using same
WO2021049819A1 (en) * 2019-09-11 2021-03-18 주식회사 엘지화학 Novel compound and organic light-emitting device comprising same
KR102446401B1 (en) * 2019-09-11 2022-09-22 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
KR20210033792A (en) * 2019-09-19 2021-03-29 삼성에스디아이 주식회사 Organic optoelectronic device and display device
US20220199915A1 (en) * 2019-10-22 2022-06-23 Lg Chem, Ltd. Compound and organic light emitting device comprising same
KR102564848B1 (en) * 2019-10-22 2023-08-08 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
KR20210061734A (en) * 2019-11-20 2021-05-28 삼성에스디아이 주식회사 Organic optoelectronic device and display device
JP2023508847A (en) * 2019-12-30 2023-03-06 エルティー・マテリアルズ・カンパニー・リミテッド HETEROCYCLE COMPOUND, ORGANIC LIGHT EMITTING DEVICE CONTAINING THE SAME, METHOD FOR PRODUCING THE SAME, AND COMPOSITION FOR ORGANIC MATERIAL LAYER
WO2021194261A1 (en) * 2020-03-26 2021-09-30 주식회사 엘지화학 Novel compound and organic light-emitting device using same
KR102344802B1 (en) * 2020-04-08 2021-12-30 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
WO2021206504A1 (en) * 2020-04-09 2021-10-14 주식회사 엘지화학 Organic light-emitting device
KR102536903B1 (en) * 2020-08-13 2023-05-26 엘티소재주식회사 Heterocyclic compound, organic light emitting device comprising same and composition for organic layer of organic light emitting device
CN114075114A (en) * 2020-08-20 2022-02-22 江苏三月科技股份有限公司 Homogeneous benzene arylamine compound and organic electroluminescent device comprising same
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CN117024287B (en) * 2023-10-10 2024-02-02 吉林奥来德光电材料股份有限公司 Light-emitting auxiliary material, preparation method thereof, organic electroluminescent device and organic electroluminescent device

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6517957B1 (en) * 1997-05-19 2003-02-11 Canon Kabushiki Kaisha Organic compound and electroluminescent device using the same
KR20130078438A (en) * 2011-12-30 2013-07-10 제일모직주식회사 Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode
WO2014067614A1 (en) * 2012-10-31 2014-05-08 Merck Patent Gmbh Electronic device
WO2015041428A1 (en) * 2013-09-17 2015-03-26 덕산네오룩스 주식회사 Organic electronic element using compound for organic electronic element and electronic device thereof
US20180145261A1 (en) * 2015-10-06 2018-05-24 Lg Chem, Ltd. Spiro-type compound and organic light emitting diode comprising same

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10203328A1 (en) 2002-01-28 2003-08-07 Syntec Ges Fuer Chemie Und Tec New triarylamine derivatives with space-filling wing groups and their use in electro-photographic and organic electroluminescent devices
JP2007059750A (en) 2005-08-26 2007-03-08 Toyo Ink Mfg Co Ltd Organic electroluminescence device material
CN1769269A (en) * 2005-09-29 2006-05-10 复旦大学 End-blocked triarylamine and carbazoles material, handling method and uses
KR101258701B1 (en) * 2005-11-24 2013-05-02 에스케이이노베이션 주식회사 Organic electroluminescent polymer having arylamine unit containing 9'-aryl-fluoren-9'-yl group and organic electroluminescent device manufactured using the same
JP5353186B2 (en) * 2007-11-30 2013-11-27 住友化学株式会社 Amine-based polymer compound and light emitting device using the same
KR20120129733A (en) * 2011-05-20 2012-11-28 (주)씨에스엘쏠라 Organic light compound and organic light device using the same
WO2014094963A1 (en) * 2012-12-21 2014-06-26 Merck Patent Gmbh Materials for organic electroluminescent devices
KR102005387B1 (en) 2013-06-05 2019-07-30 덕산네오룩스 주식회사 An organic electronic element comprising a layer for improving light efficiency, and an electronic device comprising the same
KR102417121B1 (en) * 2014-10-17 2022-07-06 삼성디스플레이 주식회사 Organic light-emitting device
KR102293436B1 (en) * 2014-11-19 2021-08-25 덕산네오룩스 주식회사 Display device using a composition for organic electronic element, and an organic electronic element thereof
CN105753629B (en) * 2015-01-07 2018-11-16 机光科技股份有限公司 Compound and the Organnic electroluminescent device for using it
CN105218541A (en) 2015-10-23 2016-01-06 上海道亦化工科技有限公司 A kind of phosphorescence host compound and organic electroluminescence device thereof
KR102595922B1 (en) * 2015-12-22 2023-10-31 삼성디스플레이 주식회사 Carbazole-based compound and organic light emitting device comprising the same
KR102635702B1 (en) 2016-01-11 2024-02-15 덕산네오룩스 주식회사 Organic light emitting diode, organic light emitting display device and compound therefor
KR102501666B1 (en) 2016-01-11 2023-02-21 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
KR101857632B1 (en) 2018-02-02 2018-05-14 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6517957B1 (en) * 1997-05-19 2003-02-11 Canon Kabushiki Kaisha Organic compound and electroluminescent device using the same
KR20130078438A (en) * 2011-12-30 2013-07-10 제일모직주식회사 Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode
WO2014067614A1 (en) * 2012-10-31 2014-05-08 Merck Patent Gmbh Electronic device
WO2015041428A1 (en) * 2013-09-17 2015-03-26 덕산네오룩스 주식회사 Organic electronic element using compound for organic electronic element and electronic device thereof
US20180145261A1 (en) * 2015-10-06 2018-05-24 Lg Chem, Ltd. Spiro-type compound and organic light emitting diode comprising same

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