WO2016129687A1 - Composé, composition, élément organique électroluminescent, et dispositif électronique - Google Patents

Composé, composition, élément organique électroluminescent, et dispositif électronique Download PDF

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WO2016129687A1
WO2016129687A1 PCT/JP2016/054181 JP2016054181W WO2016129687A1 WO 2016129687 A1 WO2016129687 A1 WO 2016129687A1 JP 2016054181 W JP2016054181 W JP 2016054181W WO 2016129687 A1 WO2016129687 A1 WO 2016129687A1
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bonded
group
carbon atom
general formula
atom bonded
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PCT/JP2016/054181
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English (en)
Japanese (ja)
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太郎 八巻
柏村　孝
池田　潔
宏典 川上
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出光興産株式会社
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/167—Electron transporting layers between the light-emitting layer and the anode
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials

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  • the present invention relates to a compound, a composition, an organic electroluminescence element, and an electronic device.
  • organic electroluminescence devices using organic substances are promising for use as solid light-emitting, inexpensive, large-area full-color display devices, and many developments have been made.
  • organic EL devices In general, an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting layer. When an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Further, the electrons recombine with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state.
  • Patent Documents 1 to 5 various compounds used for forming an organic layer have been studied in order to improve device performance.
  • An object of the present invention is to provide a compound capable of improving solubility and heat resistance. Moreover, this invention aims at providing the composition containing the said compound, providing the organic electroluminescent element containing the said compound, and providing an electronic device provided with the said organic electroluminescent element.
  • the compound which concerns on 1 aspect of this invention has the 1st structure represented by the following general formula (1), and the 2nd structure represented by the following general formula (2), and the following general formula ( 3) represented by 3), wherein the first structure, the second structure, and the third structure are each independently contained in the molecule; Furthermore, it has the 4th partial structure represented by following General formula (4), The said 4th partial structure is contained in said 1st structure, or said 1st structure, said 2nd And at least one of the third structure and the third structure.
  • X 11 to X 16 are each independently A carbon atom bonded to R 1 ; A nitrogen atom, or a carbon atom bonded to an atom contained in at least one of the second structure, the third structure, and the fourth partial structure in a molecule; At least one of X 11 to X 16 is a nitrogen atom, R 1 is a hydrogen atom or a substituent, Several R ⁇ 1 > may mutually be same or different, A plurality of R 1 may be bonded to each other to form a ring structure.
  • X 1 is a carbon atom bonded to R 2 or a carbon atom bonded to X 2
  • X 2 is a carbon atom bonded to R 3 or a carbon atom bonded to X 1
  • X 3 is an oxygen atom, a sulfur atom, a nitrogen atom, or a carbon atom bonded to R X and R Y
  • R X and R Y are each independently a hydrogen atom or a substituent
  • the nitrogen atom in X 3 is Combined with R 4 , Or bonded to an atom contained in at least one of the first structure, the third structure, and the fourth partial structure in the molecule
  • X 4 is a carbon atom bonded to R 5 or a carbon atom bonded to X 5
  • X 5 is a carbon atom bonded to R 6 or a carbon atom bonded to X 4 ;
  • at least one of the combination of X 1 and X 2 and the combination of X 4 and X 5 is
  • L bondsed to an atom contained in at least one of the structures, or bonded to a substituent, L as a substituted or unsubstituted aromatic hydrocarbon group may be bonded to Y 9 or Y 16 to form a ring structure;
  • Y 1 to Y 8 are each independently A carbon atom bonded to R 7 ;
  • Yes, Y 9 to Y 16 are each independently A carbon atom bonded to R 8 ;
  • Yes, Y 9 or Y 16 may combine with L as a substituted or un
  • X 6 is A nitrogen atom bonded to R 9 , or a nitrogen atom bonded to an atom contained in at least one of the first structure, the second structure, and the fourth partial structure in the molecule;
  • R 9 is a hydrogen atom or a substituent,
  • Z 1 to Z 8 are each independently A carbon atom bonded to R 10 , or a carbon atom bonded to an atom contained in at least one of the first structure, the second structure, and the fourth partial structure in a molecule;
  • R 10 is a hydrogen atom or a substituent,
  • the plurality of R 10 may be the same as or different from each other, n is the number of the third structure in the molecule, and is 0 or an integer of 1 or more. m + n is an integer of 2 or more.
  • X 7 and X 8 are each independently A carbon atom bonded to R 11 ; A nitrogen atom, or a carbon atom bonded to an atom contained in at least one of the first structure, the second structure, and the third structure in a molecule; R 11 is a hydrogen atom or a substituent, Ar 1 to Ar 4 are each independently A substituted or unsubstituted aromatic hydrocarbon group, A substituted or unsubstituted heterocyclic group, A first structure represented by the general formula (1), A substituted or unsubstituted aromatic hydrocarbon group bonded to an atom contained in at least one of the first structure, the second structure, and the third structure in the molecule; or the first structure in the molecule Or a substituted or unsubstituted heterocyclic group bonded to an atom contained in at least one of the second structure and the third structure. )
  • composition according to one embodiment of the present invention includes the above-described compound according to one embodiment of the present invention and a solvent.
  • the organic electroluminescent element according to one embodiment of the present invention includes an anode, an organic layer, and a cathode, and the organic layer includes the compound according to one embodiment of the present invention described above.
  • An electronic apparatus includes the organic electroluminescence element according to the above-described aspect of the present invention.
  • a compound that can improve solubility and heat resistance can be provided.
  • the composition containing the said compound, the organic electroluminescent element containing the said compound can be provided, and an electronic device provided with the said organic electroluminescent element can be provided.
  • the compound according to the present embodiment has a first structure represented by the following general formula (1) and a second structure represented by the following general formula (2), and the following general formula (3) And the first structure, the second structure, and the third structure are each independently contained in the molecule, and It has a fourth partial structure represented by the following general formula (4), and the fourth partial structure is included in the first structure, or the first structure and the second structure. And at least one of the third structures.
  • X 11 to X 16 are each independently A carbon atom bonded to R 1 ; A nitrogen atom, or a carbon atom bonded to an atom contained in at least one of the second structure, the third structure, and the fourth partial structure in a molecule; At least one of X 11 to X 16 is a nitrogen atom, R 1 is a hydrogen atom or a substituent, Several R ⁇ 1 > may mutually be same or different, A plurality of R 1 may be bonded to each other to form a ring structure.
  • X 1 is a carbon atom bonded to R 2 or a carbon atom bonded to X 2 ;
  • X 2 is a carbon atom bonded to R 3 or a carbon atom bonded to X 1 ;
  • X 3 is an oxygen atom, a sulfur atom, a nitrogen atom, or a carbon atom bonded to R X and R Y ;
  • R X and R Y are each independently a hydrogen atom or a substituent,
  • the nitrogen atom in X 3 is Combined with R 4 , Or bonded to an atom contained in at least one of the first structure, the third structure, and the fourth partial structure in the molecule;
  • X 4 is a carbon atom bonded to R 5 or a carbon atom bonded to X 5 ;
  • X 5 is a carbon atom bonded to R 6 or a carbon atom bonded to X 4 ;
  • L bondsed to an atom contained in at least one of the structures, or bonded to a substituent, L as a substituted or unsubstituted aromatic hydrocarbon group may be bonded to Y 9 or Y 16 to form a ring structure;
  • Y 1 to Y 8 are each independently A carbon atom bonded to R 7 ;
  • Yes, Y 9 to Y 16 are each independently A carbon atom bonded to R 8 ;
  • Yes, Y 9 or Y 16 may combine with L as a substituted or un
  • the plurality of second structures may be the same as or different from each other.
  • the plurality of second structures are independently bonded to any one of the first structure, the third structure, and the fourth partial structure.
  • Each of the plurality of second structures is preferably bonded to the first structure.
  • X 6 is A nitrogen atom bonded to R 9 , or a nitrogen atom bonded to an atom contained in at least one of the first structure, the second structure, and the fourth partial structure in the molecule;
  • R 9 is a hydrogen atom or a substituent,
  • Z 1 to Z 8 are each independently A carbon atom bonded to R 10 , or a carbon atom bonded to an atom contained in at least one of the first structure, the second structure, and the fourth partial structure in a molecule;
  • R 10 is a hydrogen atom or a substituent,
  • the plurality of R 10 may be the same as or different from each other, n is the number of the third structure in the molecule, and is 0 or an integer of 1 or more. m + n is an integer of 2 or more.
  • X 7 and X 8 are each independently A carbon atom bonded to R 11 ; A nitrogen atom, or a carbon atom bonded to an atom contained in at least one of the first structure, the second structure, and the third structure in a molecule; R 11 is a hydrogen atom or a substituent, Ar 1 to Ar 4 are each independently A substituted or unsubstituted aromatic hydrocarbon group, A substituted or unsubstituted heterocyclic group, A first structure represented by the general formula (1), A substituted or unsubstituted aromatic hydrocarbon group bonded to an atom contained in at least one of the first structure, the second structure, and the third structure in the molecule; or the first structure in the molecule Or a substituted or unsubstituted heterocyclic group bonded to an atom contained in at least one of the second structure and the third structure.
  • the first structure represented by the general formula (1) includes the fourth partial structure represented by the general formula (4). Also good.
  • X 1 to X 6 , X 7 to X 8 , X 11 to X 16 , Y 1 to Y 16 , Z 1 to Z 8 , Ar 1 to Ar 4 , L, m, n, and p are: X 11 to X 16 in the general formula (1), X 3 to X 5 , Y 1 to Y 16 , L, m, and p in the general formula (2), X 6 and Z in the general formula (3) 1 to Z 8 and n, and X 7 to X 8 and Ar 1 to Ar 4 in the general formula (4) have the same meanings, respectively.
  • the 6-membered ring containing X 7 and X 8 in the general formula (4) is preferably a 6-membered ring containing X 11 to X 16 in the general formula (1).
  • X 11 is preferably a carbon atom bonded to Ar 1 ;
  • X 12 is preferably a carbon atom bonded to Ar 2 ,
  • X 13 is preferably X 8 ;
  • X 14 is preferably a carbon atom bonded to Ar 3 ;
  • X 15 is preferably X 7 ;
  • X 16 is preferably a carbon atom bonded to Ar 4 .
  • the first structure is preferably a structure represented by the following general formula (11).
  • X 11 ⁇ X 16 and Ar 1 ⁇ Ar 4 is a Ar 1 ⁇ Ar 4 in the general formula (1) in X 11 ⁇ X 16 and the formula (4), respectively the same It is.
  • At least one of X 15 as X 7 and X 13 as X 8 is a nitrogen atom.
  • X 13 and X 15 are preferably nitrogen atoms.
  • Examples of the structure represented by the general formula (11) include the following structures.
  • At least two of Ar 1 to Ar 4 are A substituted or unsubstituted aromatic hydrocarbon group bonded to an atom contained in at least one of the second structure and the third structure in the molecule; or the second structure in the molecule, and the first A substituted or unsubstituted heterocyclic group bonded to an atom included in at least one of the three structures is preferable.
  • the first structure includes the fourth partial structure,
  • the structure represented by the general formula (1) is also preferably at least one of Ar 1 to Ar 4 in the general formula (4). That is, the first structure is preferably represented by any of the following general formulas (141) to (143).
  • X 7 ⁇ X 8, and X 12 ⁇ X 16 is, X 7 in X 12-X 16, and the formula in the formula (1) (4) - X 8 is the same as X 8, and X 11 is a carbon atom bonded to the fourth partial structure.
  • Ar 2 ⁇ Ar 4 is a Ar 2 ⁇ Ar 4 in the general formula (4), which is the same meaning.
  • Ar 1, Ar 3, and Ar 4 Ar 1, Ar 3 in the general formula (4), and the Ar 4, which is the same meaning.
  • Ar 1, Ar 2, and Ar 4 are the Ar 1, Ar 2, and Ar 4 in the general formula (4), which is the same meaning
  • X 7 and X 8 are carbon atoms bonded to R 11 , At least one of X 12 to X 16 is preferably a nitrogen atom.
  • X 12 to X 16 are each independently A carbon atom bonded to R 1 ; It is preferably a nitrogen atom or a carbon atom bonded to an atom contained in at least one of the second structure and the third structure in the molecule, At least one of X 12 to X 16 is preferably a nitrogen atom, At least one of X 12 to X 16 is preferably a carbon atom bonded to an atom contained in at least one of the second structure and the third structure in the molecule.
  • two or three of X 12 to X 16 are preferably nitrogen atoms, and at least two of X 12 , X 14 , and X 16 are nitrogen atoms. It is more preferable.
  • Examples of the structures represented by the general formulas (141) to (143) include the following structures.
  • the first structure includes the fourth partial structure, It is also preferable that any of Ar 1 to Ar 4 is bonded to the ring containing X 11 to X 16 in the general formula (1). That is, the first structure is also preferably a structure represented by the following general formula (12).
  • X 7 to X 8 , X 11 to X 16 , and Ar 1 to Ar 4 represent X 11 to X 16 in the general formula (1) and X in the general formula (4). 7 to X 8 and Ar 1 to Ar 4 , respectively, provided that at least one of X 11 to X 16 is a substituted or unsubstituted aromatic hydrocarbon group in Ar 1 to Ar 4 , or A carbon atom bonded to a substituted or unsubstituted heterocyclic group, * 14 represents a bond to the fourth partial structure of the first structure, and * 41 represents a bond of the fourth partial structure.
  • bond part with said 1st structure is represented.
  • X 7 and X 8 are preferably a carbon atom bonded to R 11 .
  • X 12 to X 16 are each independently A carbon atom bonded to R 1 ; It is preferably a nitrogen atom or a carbon atom bonded to an atom contained in at least one of the second structure and the third structure in the molecule, At least one of X 12 to X 16 is preferably a nitrogen atom. At least one of X 12 to X 16 is preferably a carbon atom bonded to an atom contained in at least one of the second structure and the third structure in the molecule.
  • the first structure includes the fourth partial structure,
  • the first structure is also preferably represented by any one of the following general formulas (144) to (146).
  • X 7 to X 8 , X 11 to X 16 , and Ar 1 to Ar 4 are the same as X 11 to X 16 in the general formula (1) and the general formula (1). It is synonymous with X 7 to X 8 and Ar 1 to Ar 4 in 4).
  • X 11 is a carbon atom bonded to Ar 1
  • Ar 1 is a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group bonded to X 11.
  • X 11 is a carbon atom bonded to Ar 3
  • Ar 3 is a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group bonded to X 11.
  • X 11 is a carbon atom bonded to Ar 2
  • Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group or substituted or unsubstituted heterocyclic group bonded to X 11. It is preferable that
  • X 7 and X 8 are preferably a carbon atom bonded to R 11 .
  • X 12 to X 16 are each independently A carbon atom bonded to R 1 ; It is preferably a nitrogen atom or a carbon atom bonded to an atom contained in at least one of the second structure and the third structure in the molecule, At least one of X 12 to X 16 is preferably a nitrogen atom. At least one of X 12 to X 16 is preferably a carbon atom bonded to an atom contained in at least one of the second structure and the third structure in the molecule.
  • Examples of the structures represented by the general formulas (144) to (146) include the following structures.
  • the sum of m and n (m + n) is preferably an integer of 2 or more and 4 or less.
  • n is preferably 0.
  • the second structure represented by the general formula (2) is preferably represented by the following general formula (20).
  • X 3 , Y 1 to Y 8 , Y 9 to Y 16 , L, m, and p are the same as X 3 , Y 1 to Y 8 , Y 9 to Y in the general formula (2).
  • Y 16 , L, m, and p have the same meanings
  • X 1 and X 2 are carbon atoms that are bonded to each other
  • X 4 and X 5 are carbon atoms that are bonded to each other.
  • p is preferably 1, Any one of Y 1 to Y 8 is preferably a carbon atom bonded to any of Y 13 to Y 16 ; Any of Y 13 to Y 16 is preferably a carbon atom bonded to any of Y 1 to Y 8 .
  • L is a substituted or unsubstituted aromatic hydrocarbon group having 6 ring-forming carbon atoms
  • Y 16 is a carbon atom bonded to L
  • L and Y 16 are preferably bonded to form a ring structure. That is, the second structure represented by the general formula (2) is also preferably represented by the following general formula (21).
  • X 3 , Y 1 to Y 8 , Y 9 to Y 16 , m, and p are X 3 , Y 1 to Y 8 , Y 9 to Y 16 in the general formula (2).
  • any of Y 1 to Y 8 and X 3 is a carbon atom or a nitrogen atom bonded to an aromatic hydrocarbon group that is L, and X 1 and X 2 is a carbon atom bonded to each other, X 4 is a carbon atom bonded to R 5 , X 5 is a carbon atom bonded to R 6 , and R 5 to R 6 are each represented by the general formula R 5 to R 6 in (2) have the same meanings, R 12 is a hydrogen atom or a substituent, and s is 3.
  • the plurality of R 12 may be the same or different.
  • p is preferably an integer of 1 or more and 3 or less.
  • the second structure represented by the general formula (2) is also preferably represented by the following general formula (22).
  • Y 1 to Y 8 and any of X 3 are a carbon atom or a nitrogen atom bonded to L
  • X 1 and X 2 are a carbon atom bonded to each other
  • X 4 and X 5 is a carbon atom bonded to each other.
  • p is preferably 2
  • X 3 is, A nitrogen atom bonded to R 4 or a nitrogen atom bonded to an atom included in at least one of the first structure, the third structure, and the fourth partial structure in the molecule
  • Y 1 to Y 8 are each independently A carbon atom bonded to R 7
  • Y 9 to Y 16 are each independently It is preferably a carbon atom bonded to R 8 or a carbon atom bonded to an atom contained in at least one of the first structure, the third structure, and the fourth partial structure in the molecule.
  • the second structure represented by the general formula (2) is also preferably represented by the following general formula (23).
  • Y 1 to Y 8 and X 3 are carbon atoms or nitrogen atoms bonded to L
  • X 1 and X 2 are carbon atoms bonded to each other
  • X 4 is , R 5, and X 5 is a carbon atom bonded to R 6 .
  • X 3 is, A nitrogen atom bonded to R 4 or a nitrogen atom bonded to an atom included in at least one of the first structure, the third structure, and the fourth partial structure in the molecule; Any of Y 1 to Y 8 is preferably a carbon atom bonded to L.
  • the second structure represented by the general formula (2) is also preferably represented by the following general formula (24).
  • X 3, Y 1 ⁇ Y 16, and m is an X 3, Y 1 ⁇ Y 16 , and m in the formula (2), have the same meanings, Y a ⁇ Y h is synonymous with Y 9 to Y 16 in the general formula (2), and L 21 and L 22 are each independently synonymous with L in the general formula (2), provided that Y a — Any of Y d is a carbon atom bonded to L 21 , any of Y e to Y h is a carbon atom bonded to any of Y 5 to Y 8 , and X 1 and X 2 are X 4 is a carbon atom bonded to R 5 , X 5 is a carbon atom bonded to R 6 , X a is a carbon atom bonded to X b , b is a carbon atom bonded with X a.
  • X 1 and X 2 are preferably carbon atoms bonded to each other, X 3 is, A nitrogen atom bonded to R 4 or a nitrogen atom bonded to an atom included in at least one of the first structure, the third structure, and the fourth partial structure in the molecule;
  • L 21 and L 22 are each independently synonymous with L in the general formula (2), Y a to Y d are each independently A carbon atom bonded to R 8 ; A carbon atom bonded to L 21 , or a carbon atom bonded to an atom included in at least one of the first structure, the third structure, and the fourth partial structure in the molecule;
  • Y e to Y h are each independently A carbon atom bonded to R 8 ;
  • Y 1 to Y 4 are each independently synonymous with
  • examples of the second structure include the following structures.
  • a wavy line portion represents a coupling point between the second structure and another structure.
  • examples of the third structure include the following structures.
  • a wavy line portion represents a coupling point between the third structure and another structure.
  • examples of the third structure include the following structures.
  • a plurality of R 1 are not bonded to each other and a ring structure is not formed.
  • R 1 to R 12 , R X , and R Y as substituents are each independently A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, Substituted silyl groups, Substituted germanium groups, Substituted phosphine oxide groups, Halogen atoms, A cyano group, It is preferably selected from the group consisting of a nitro group and a carboxy group.
  • R 4 and R 9 as a substituent are each independently preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms
  • R X and R Y as substituents are each independently It is preferably selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • the first structure and the second structure are bonded, and the first structure and the third structure are bonded.
  • the first structure includes the fourth partial structure
  • the second structure is preferably combined with the first structure or the fourth partial structure
  • the structure is preferably bonded to the first structure or the fourth partial structure.
  • the compound of the present embodiment is preferably represented by any of the following general formulas (100) to (104).
  • X 1 to X 5 , Y 1 to Y 16 , L, m, and p are the same as X 1 to X 5 , Y 1 to Y 16 in the general formula (2). , L, m, and p have the same meanings.
  • X 11 to X 16 and Ar 1 to Ar 4 are X 11 to X 16 in the general formula (1), and Ar 1 to Ar 4 in the general formula (4), respectively.
  • * 12 represents the coupling
  • * 21 represents the coupling
  • X 7 to X 8 , X 12 to X 16 , and Ar 2 to Ar 4 represent X 12 to X 16 in the general formula (1) and X in the general formula (4).
  • 7 to X 8 and Ar 2 to Ar 4 have the same meanings.
  • * 12 represents a joint portion of the first structure or the fourth partial structure with the second structure
  • * 21 is the first structure or the fourth part of the second structure. Represents the connection with the structure.
  • X 7 to X 8 , X 12 to X 16 , Ar 1 , Ar 3 , and Ar 4 represent X 12 to X 16 in the general formula (1) and the general formula (4).
  • X 7 to X 8 , Ar 1 , Ar 3 , and Ar 4 have the same meanings.
  • * 12 represents a joint portion of the first structure or the fourth partial structure with the second structure, and * 21 is the first structure or the fourth part of the second structure. Represents the connection with the structure.
  • X 7 to X 8 , X 12 to X 16 , Ar 1 , Ar 2 , and Ar 4 represent X 12 to X 16 in the general formula (1) and the general formula (4).
  • X 7 to X 8 , Ar 1 , Ar 2 , and Ar 4 have the same meanings.
  • * 12 represents a joint portion of the first structure or the fourth partial structure with the second structure, and * 21 is the first structure or the fourth part of the second structure.
  • X 7 to X 8 , X 11 to X 16 , and Ar 1 to Ar 4 represent X 11 to X 16 in the general formula (1) and X in the general formula (4).
  • 7 to X 8 and Ar 1 to Ar 4 have the same meanings.
  • * 12 represents a joint portion of the first structure or the fourth partial structure with the second structure, and * 21 is the first structure or the fourth part of the second structure.
  • * 14 represents a coupling portion with the fourth partial structure of the first structure, and * 41 represents a coupling portion with the first structure of the fourth partial structure. Represents a part.
  • the compound which concerns on this embodiment can be manufactured by the method as described in the Example mentioned later, for example.
  • the compound according to the present embodiment can be produced by following the methods described in the examples and using known alternative reactions and raw materials tailored to the target product.
  • the compound of this embodiment is excellent in solubility and heat resistance.
  • the composition of this embodiment contains the compound which concerns on one Embodiment of this invention, and a solvent.
  • the solvent is preferably an organic solvent.
  • the organic solvent include chlorinated solvents (for example, chloroform, chlorobenzene, chlorotoluene, chloroxylene, chloroanisole, dichloromethane, dichlorobenzene, dichlorotoluene, dichloroethane, trichloroethane, trichlorobenzene, trichloromethylbenzene, bromobenzene, dibromobenzene.
  • ether solvents eg, tetrahydrofuran, dioxane, dioxolane, oxazole, methylbenzoxazole, benzisoxazole, furan, furazane, benzofuran, and dihydrobenzofuran
  • aromatic hydrocarbon solvents eg, Ethylbenzene, diethylbenzene, triethylbenzene, trimethylbenzene, trimethoxybenzene, propylbenzene, iso Lopylbenzene, diisopropylbenzene, dibutylbenzene, amylbenzene, dihexylbenzene, cyclohexylbenzene, tetramethylbenzene, dodecylbenzene, benzonitrile, acetophenone, methylacetophenone, methoxyacetophenone, toluic acid ethyl ester, toluene,
  • aromatic hydrocarbon solvents
  • Ketone solvents eg, acetone, methyl ethyl ketone, cyclohexanone, and acetophenone
  • ester solvents eg, ethyl acetate, butyl acetate, ethyl cellosolve acetate
  • Methyl benzoate ethyl benzoate
  • phenyl acetate polyhydric alcohols and derivatives thereof (for example, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, Triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol), alcohol solvents (eg, methanol, ethanol, propanol, isopropanol, and cyclohexanol), sulfoxide solvents (eg, dimethyl sul
  • composition of this embodiment may contain other materials in addition to the compound and solvent of this embodiment.
  • composition which concerns on one Embodiment of this invention can be used suitably as an organic EL element material.
  • the configuration of the organic EL element according to this embodiment will be described.
  • the organic EL element includes an anode, an organic layer, and a cathode.
  • the organic layer includes one or more layers composed of an organic compound.
  • the organic layer may further contain an inorganic compound.
  • at least one of the organic layers includes the compound according to the present embodiment.
  • the “light emitting layer” is an organic layer having a light emitting function.
  • the “hole injection / transport layer” means “at least one of a hole injection layer and a hole transport layer”.
  • the “electron injection / transport layer” means “at least one of an electron injection layer and an electron transport layer”.
  • a hole injection layer is provided between the hole transport layer and the anode.
  • each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be composed of a single layer or a plurality of layers.
  • the organic layer preferably includes a light emitting layer, and the light emitting layer preferably includes the compound of the present embodiment.
  • FIG. 1 schematic structure of an example of the organic EL element in this embodiment is shown.
  • the organic EL element 1 includes a translucent substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4.
  • the organic layer 10 includes a light emitting layer 7, a hole injection layer 5 provided between the anode 3 and the light emitting layer 7, and a hole transport layer 6 provided between the hole injection layer 5 and the light emitting layer 7.
  • an electron transport zone 11 provided between the light emitting layer 7 and the cathode 4.
  • the electron transport zone 11 includes an electron transport layer 8 and an electron injection layer 9.
  • the light emitting layer 7 contains the compound which concerns on one Embodiment of this invention.
  • the light emitting layer 7 of the organic EL element 1 includes at least the compound according to one embodiment of the present invention.
  • the content of the compound according to an embodiment of the present invention is preferably 0.1% by mass or more and 1% by mass or more and 99.9% by mass or less. More preferably, the content is 5% by mass or more and 95% by mass or less.
  • the organic EL device 1 of the present embodiment does not exclude that the light emitting layer 7 contains a material other than the compound according to one embodiment of the present invention.
  • the light emitting layer 7 may include a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence as a light emitting material.
  • a fluorescent compound is a compound that can emit light from a singlet excited state
  • a phosphorescent compound is a compound that can emit light from a triplet excited state.
  • blue fluorescent materials that can be used for the light emitting layer 7 include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives.
  • N, N′-bis [4- (9H-carbazol-9-yl) phenyl] -N, N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S)
  • 4- (9H -Carbazol-9-yl) -4 '-(10-phenyl-9-anthryl) triphenylamine (abbreviation: YGAPA)
  • 4- (10-phenyl-9-anthryl) -4'-(9-phenyl- 9H-carbazol-3-yl) triphenylamine abbreviation: PCBAPA
  • an aromatic amine derivative or the like can be used as the green fluorescent material that can be used for the light emitting layer 7, for example.
  • an aromatic amine derivative or the like can be used.
  • red fluorescent materials that can be used for the light-emitting layer 7 include tetracene derivatives and diamine derivatives. Specifically, N, N, N ′, N′-tetrakis (4-methylphenyl) tetracene-5,11-diamine (abbreviation: p-mPhTD) and 7,14-diphenyl-N, N, N ′ , N′-tetrakis (4-methylphenyl) acenaphtho [1,2-a] fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), and the like.
  • p-mPhTD N, N ′, N′-tetrakis (4-methylphenyl) tetracene-5,11-diamine
  • p-mPhTD N, N ′, N′-tetrakis (4-methylphenyl) acenaphtho [1,2-a] fluoranthene-3,
  • a metal complex such as an iridium complex, an osmium complex, and a platinum complex is used.
  • a metal complex such as an iridium complex, an osmium complex, and a platinum complex
  • a metal complex such as an iridium complex, an osmium complex, and a platinum complex.
  • FIr6 bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) picolinate
  • FIr (pic) bis [2- (3 ′, 5′bistrifluoromethylphenyl) pyridinato-N, C2 ′] Iridium (III) picolinate
  • Ir (CF 3 ppy) 2 (pic) bis [2- (4 ′, 6′-difluorophen
  • an iridium complex or the like is used as the green phosphorescent material that can be used for the light emitting layer 7, for example.
  • red phosphorescent materials that can be used for the light emitting layer 7 include metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes.
  • metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes.
  • Ir (btp) 2 (acac) bis [2- (2′-benzo [4,5- ⁇ ] thienyl) pyridinato-N, C3 ′] iridium (III) acetylacetonate
  • Ir (btp) 2 (acac) bis (1-phenylisoquinolinato-N, C2 ′) iridium (III) acetylacetonate
  • Ir (piq) 2 (acac) acetylacetonato
  • the film thickness of the light emitting layer 7 in the organic EL element 1 of this embodiment becomes like this.
  • they are 5 nm or more and 50 nm or less, More preferably, they are 7 nm or more and 50 nm or less, More preferably, they are 10 nm or more and 50 nm or less. If it is 5 nm or more, the light emitting layer 7 can be formed easily and the chromaticity can be easily adjusted. Moreover, if it is 50 nm or less, the raise of a drive voltage can be suppressed.
  • the substrate 2 is used as a support for the organic EL element 1.
  • the substrate 2 for example, glass, quartz, plastic, or the like can be used.
  • a flexible substrate may be used.
  • a flexible substrate is a substrate that can be bent (flexible), such as polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, or polyethylene naphthalate. And a plastic substrate.
  • an inorganic vapor deposition film can also be used.
  • anode For the anode 3 formed on the substrate 2, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, And graphene.
  • ITO indium tin oxide
  • ITO indium oxide-tin oxide containing silicon or silicon oxide
  • indium oxide-zinc oxide indium oxide containing tungsten oxide and zinc oxide
  • graphene graphene.
  • Au gold
  • platinum (Pt) nickel
  • Ni tungsten
  • W chromium
  • Mo molybdenum
  • iron (Fe) iron
  • cobalt Co
  • copper copper
  • Pd palladium
  • Ti titanium
  • a metal material nitride for example, titanium nitride
  • indium oxide containing tungsten oxide and zinc oxide contains 0.5% by mass to 5% by mass of tungsten oxide and 0.1% by mass to 1% by mass of zinc oxide with respect to indium oxide.
  • a target it can be formed by a sputtering method.
  • the hole injection layer 5 formed in contact with the anode 3 is made of a composite material that facilitates hole injection regardless of the work function of the anode 3.
  • a material that can be used as an electrode material for example, a metal, an alloy, an electrically conductive compound, and a mixture thereof, and other elements belonging to Group 1 or Group 2 of the periodic table
  • an element belonging to Group 1 or Group 2 of the periodic table which is a material having a low work function, that is, an alkali metal such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca), and strontium Alkaline earth metals such as (Sr) and alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these can also be used.
  • an alkali metal such as lithium (Li) and cesium (Cs)
  • strontium Alkaline earth metals such as (Sr) and alloys containing these (for example, MgAg, AlLi)
  • rare earth metals such as euro
  • anode 3 when forming the anode 3 using an alkali metal, an alkaline earth metal, and an alloy containing these, a vacuum evaporation method and a sputtering method can be used. Further, when a silver paste or the like is used, a coating method or an ink jet method can be used.
  • the hole injection layer 5 is a layer containing a substance having a high hole injection property.
  • Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, or the like can be used.
  • As a substance having a high hole-injecting property 4,4 ′, 4 ′′ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, which is a low-molecular organic compound, is used.
  • a high molecular compound an oligomer, a dendrimer, a polymer, or the like
  • a high molecular compound an oligomer, a dendrimer, a polymer, or the like
  • PVK poly (N-vinylcarbazole)
  • PVTPA poly (4-vinyltriphenylamine)
  • PTPDMA poly [N- (4- ⁇ N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino ⁇ phenyl) methacrylamide]
  • PTPDMA poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine]
  • Poly-TPD Poly-TPD
  • a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly (styrenesulfonic acid) (PAni / PSS) is added can also be used.
  • the hole transport layer 6 is a layer containing a substance having a high hole transport property.
  • An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer 6.
  • NPB 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • TPD diphenyl- [1,1′-biphenyl] -4,4′-diamine
  • BAFLP 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine
  • the substances mentioned here are mainly substances having a hole mobility of 10 ⁇ 6 cm 2 / (V ⁇ s) or more.
  • the hole transport layer 6 includes CBP, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3- [4- (10-phenyl-9-anthryl).
  • a carbazole derivative such as phenyl] -9H-carbazole (PCzPA) or an anthracene derivative such as t-BuDNA, DNA, or DPAnth may be used.
  • a high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK poly (N-vinylcarbazole)
  • PVTPA poly (4-vinyltriphenylamine)
  • any substance other than these may be used as long as it has a property of transporting more holes than electrons.
  • the layer containing a substance having a high hole-transport property is not limited to a single layer, and may be a layer in which two or more layers containing the above substances are stacked. When two or more hole transport layers are arranged, it is preferable to arrange a layer containing a material having a larger energy gap on the side closer to the light emitting layer 7.
  • the hole transport layer 6 has a function of preventing triplet excitons generated in the light emitting layer 7 from diffusing into the hole transport layer and confining the triplet excitons in the light emitting layer 7. Is preferred.
  • the electron transport layer 8 is a layer containing a substance having a high electron transport property.
  • the electron transport layer 8 includes 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3 ) High molecular compounds can be used.
  • Alq tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq 3 ), bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviation: BeBq 2 ), Metal complexes such as BAlq, Znq, ZnPBO, and ZnBTZ can be used.
  • a benzimidazole compound can be suitably used.
  • the substances described here are mainly substances having an electron mobility of 10 ⁇ 6 cm 2 / (V ⁇ s) or more.
  • a substance other than the above may be used as the electron transport layer 8 as long as the substance has a higher electron transport property than the hole transport property.
  • the electron transport layer 8 is not limited to a single layer, and may be a layer in which two or more layers made of the above substances are stacked.
  • a polymer compound can be used for the electron transport layer 8.
  • poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py)
  • poly [(9,9-dioctylfluorene- 2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) or the like can be used.
  • the electron transport layer 8 prevents triplet excitons generated in the light emitting layer 7 from diffusing into the electron transport layer 8 and the electron injection layer 9 and confines the triplet excitons in the light emitting layer 7. It preferably has a function.
  • the electron injection layer 9 is a layer containing a substance having a high electron injection property.
  • the electron injection layer 9 includes lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), and lithium oxide (LiOx).
  • alkaline earth metals, or compounds thereof can be used.
  • a substance in which an alkali metal, an alkaline earth metal, or a compound thereof is contained in a substance having an electron transporting property specifically, a substance in which magnesium (Mg) is contained in Alq may be used. In this case, electron injection from the cathode 4 can be performed more efficiently.
  • a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer 9.
  • a composite material is excellent in electron injecting property and electron transporting property because electrons are generated in the organic compound by the electron donor.
  • the organic compound is preferably a material excellent in transporting the generated electrons.
  • a substance (metal complex, heteroaromatic compound, etc.) constituting the electron transport layer 8 described above is used.
  • the electron donor may be any substance that exhibits an electron donating property to the organic compound.
  • an alkali metal, an alkaline earth metal, or a rare earth metal is preferable, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium.
  • Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given.
  • a Lewis base such as magnesium oxide can also be used.
  • an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
  • cathode For the cathode 4, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less).
  • a cathode material include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca). And alkaline earth metals such as strontium (Sr), and alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these .
  • the cathode 4 when forming the cathode 4 using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Moreover, when using a silver paste etc., the apply
  • the method for forming each layer of the organic EL element 1 of the present embodiment is not limited except as specifically mentioned above.
  • known methods such as a dry film forming method and a wet film forming method can be employed.
  • the dry film forming method include a vacuum deposition method, a molecular beam deposition method (MBE method), a sputtering method, a plasma method, and an ion plating method.
  • wet film forming method examples include spin coating, dipping, flow coating, casting, bar coating, roll coating, ink jet, and printing (for example, letterpress printing, intaglio printing, lithographic printing) Stencil printing method, and printing method combining them with offset printing method), inkjet printing method, spray coating method, slit coating method, cap coating method, gravure roll coating method, meniscus coating method and the like.
  • the light emitting layer containing the compound according to one embodiment of the present invention is a solution containing a solvent and the compound according to one embodiment of the present invention (hereinafter also referred to as “coating liquid”). Is preferably formed by a coating method.
  • the coating liquid may contain other materials such as a light emitting material as necessary.
  • a wet film forming method is preferably used.
  • a printing method, an ink jet printing method, a dispenser coating, and the like are preferable.
  • a method is used in which the compound according to one embodiment of the present invention is formed on the transfer precursor substrate by the wet film formation method, and then transferred onto the wiring substrate having the target electrode by laser light, heat press or the like. You can also. Film formation by these methods can be performed under conditions well known to those skilled in the art, and details thereof are omitted.
  • the coating solution used in the coating method only needs to contain at least one compound according to one embodiment of the present invention, and may be dissolved or dispersed in a solvent.
  • the content of the compound according to an embodiment of the present invention in the coating solution is preferably 0.1 to 15% by mass, and more preferably 0.5 to 10% by mass with respect to the entire film-forming solution.
  • a solvent the organic solvent similar to the solvent in the composition which concerns on one Embodiment of this invention can be mentioned.
  • organic solvents at least from the viewpoint of solubility, film formation uniformity, viscosity characteristics, etc., at least toluene, xylene, ethylbenzene, amylbenzene, anisole, 4-methoxytoluene, 2-methoxytoluene, 1,2- It preferably contains at least one of dimethoxybenzene, mesitylene, tetrahydronaphthalene, cyclohexylbenzene, 2,3-dihydrobenzofuran, cyclohexanone, and methylcyclohexanone.
  • the organic solvent used in the coating solution preferably has a boiling point of 110 ° C. or higher and a solubility in water at 20 ° C. of 1% by mass or less, and is a compound represented by the following general formula (5). More preferred.
  • R represents a substituent having 1 to 20 carbon atoms, and u represents an integer of 0 to 6.
  • a plurality of R may be the same or different from each other.
  • the coating solution for forming a film includes the compound according to an embodiment of the present invention and a solvent having a boiling point of 110 ° C. or higher and a solubility in water at 20 ° C. of 1% by mass or less. It is preferable to contain the compound represented by these. Moreover, you may add an additive to the coating liquid for film-forming as needed. Examples of the additive include a viscosity adjusting agent, a surface tension adjusting agent, a crosslinking reaction initiator, and a crosslinking reaction catalyst. The additive is preferably selected from those that do not affect the device characteristics even if they remain in the film, or those that can be removed from the film in the film formation step.
  • the film thickness of each organic layer of the organic EL element 1 of the present embodiment is not limited except as specifically mentioned above. Usually, the film thickness is preferably in the range of several nm to 1 ⁇ m because defects such as pinholes are unlikely to occur and the efficiency is improved at a low applied voltage.
  • the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in the atom.
  • the carbon contained in the substituent is not included in the number of ring-forming carbons.
  • the “ring-forming carbon number” described below is the same unless otherwise specified.
  • the benzene ring has 6 ring carbon atoms
  • the naphthalene ring has 10 ring carbon atoms
  • the pyridinyl group has 5 ring carbon atoms
  • the furanyl group has 4 ring carbon atoms.
  • the carbon number of the alkyl group is not included in the number of ring-forming carbons.
  • the carbon number of the fluorene ring as a substituent is not included in the number of ring-forming carbons.
  • the number of ring-forming atoms means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocycle) having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly).
  • the ring compound represents the number of atoms constituting the ring itself.
  • An atom that does not constitute a ring for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring
  • an atom contained in a substituent when the ring is substituted by a substituent is not included in the number of ring-forming atoms.
  • the “number of ring-forming atoms” described below is the same unless otherwise specified.
  • the pyridine ring has 6 ring atoms
  • the quinazoline ring has 10 ring atoms
  • the furan ring has 5 ring atoms.
  • a hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms. Further, when, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.
  • each substituent described in the general formula will be described.
  • Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms (sometimes referred to as an aryl group) in the present embodiment include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, and a phenanthryl group.
  • the aryl group preferably has 6 to 20 ring carbon atoms, more preferably 6 to 14, and still more preferably 6 to 12.
  • aryl groups a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group are particularly preferable.
  • the 9-position carbon atom is substituted or unsubstituted alkyl group having 1 to 30 carbon atoms in the present embodiment described later or a substituted group.
  • an unsubstituted aryl group having 6 to 18 ring carbon atoms is preferably substituted.
  • the heterocyclic group having 5 to 30 ring atoms (sometimes referred to as a heteroaryl group, a heteroaromatic ring group, or an aromatic heterocyclic group) is a nitrogen atom or a sulfur atom as a heteroatom.
  • heterocyclic group having 5 to 30 ring atoms in the present embodiment examples include a pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolinyl group, naphthyridinyl group, phthalazinyl group, quinoxalinyl group, Quinazolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, benzimidazolyl group, indazolyl group, imidazolpyridinyl group, benz Triazolyl, carbazolyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazo
  • the number of ring-forming atoms of the heterocyclic group is preferably 5-20, and more preferably 5-14.
  • the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in the present embodiment or substitution is performed on the 9th-position nitrogen atom.
  • an unsubstituted heterocyclic group having 5 to 30 ring atoms is preferably substituted.
  • the heterocyclic group may be a group derived from a partial structure represented by the following general formulas (XY-1) to (XY-18), for example.
  • X and Y are each independently a hetero atom, preferably an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, or a germanium atom.
  • the partial structures represented by the general formulas (XY-1) to (XY-18) have a bond at an arbitrary position to be a heterocyclic group, and this heterocyclic group has a substituent. Also good.
  • the carbazolyl group may include, for example, a group in which a ring is further condensed with respect to a carbazole ring represented by the following formula. Such a group may also have a substituent. Further, the position of the bond (dashed line portion) can be changed as appropriate.
  • the alkyl group having 1 to 30 carbon atoms may be linear, branched or cyclic.
  • the linear or branched alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl
  • the linear or branched alkyl group in the present embodiment preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.
  • An amyl group, an isoamyl group, and a neopentyl group are particularly preferable.
  • Examples of the cycloalkyl group having 3 to 30 carbon atoms in the present embodiment include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, an adamantyl group, and a norbornyl group.
  • the number of carbon atoms forming the ring of the cycloalkyl group is preferably 3 to 10, and more preferably 5 to 8.
  • a cyclopentyl group and a cyclohexyl group are particularly preferable.
  • halogenated alkyl group in which the alkyl group is substituted with a halogen atom examples include a fluoroalkyl group in which the alkyl group having 1 to 30 carbon atoms is substituted with one or more halogen atoms. Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, a trifluoroethyl group, and a pentafluoroethyl group.
  • an aralkyl group having 6 to 30 ring carbon atoms is preferable, and is represented by —Z 3 —Z 4 .
  • Z 3 include an alkylene group corresponding to the alkyl group having 1 to 30 carbon atoms.
  • this Z 4 include the above aryl group having 6 to 30 ring carbon atoms.
  • This aralkyl group is an aralkyl group having 7 to 30 carbon atoms (the aryl moiety has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms), and the alkyl moiety has 1 to 30 carbon atoms (preferably 1 to 1 carbon atoms).
  • aralkyl group examples include benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and phenyl-t-butyl.
  • ⁇ -naphthylmethyl group 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ - Examples include naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, and 2- ⁇ -naphthylisopropyl group.
  • Examples of the substituted silyl group in the present embodiment include an alkylsilyl group having 3 to 30 carbon atoms and an arylsilyl group having 6 to 30 ring carbon atoms.
  • Examples of the alkylsilyl group having 3 to 30 carbon atoms in the present embodiment include a trialkylsilyl group having an alkyl group exemplified as the alkyl group having 1 to 30 carbon atoms, specifically, a trimethylsilyl group and a triethylsilyl group.
  • the three alkyl groups in the trialkylsilyl group may be the same or different.
  • Examples of the arylsilyl group having 6 to 30 ring carbon atoms in the present embodiment include a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group.
  • Examples of the dialkylarylsilyl group include a dialkylarylsilyl group having two alkyl groups exemplified as the alkyl group having 1 to 30 carbon atoms and one aryl group having 6 to 30 ring carbon atoms. .
  • the carbon number of the dialkylarylsilyl group is preferably 8-30.
  • alkyldiarylsilyl group examples include an alkyldiarylsilyl group having one alkyl group exemplified for the alkyl group having 1 to 30 carbon atoms and two aryl groups having 6 to 30 ring carbon atoms. .
  • the alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.
  • Examples of the triarylsilyl group include a triarylsilyl group having three aryl groups having 6 to 30 ring carbon atoms.
  • the carbon number of the triarylsilyl group is preferably 18-30.
  • the substituted germanium group in this embodiment is preferably represented by —Ge (R 101 ) 3 .
  • R 101 is each independently a substituent.
  • Substituent R 101 is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
  • the plurality of R 101 may be the same as or different from each other.
  • the substituted phosphine oxide group in the present embodiment is preferably represented by the following general formula (200).
  • R 102 and R 103 are each independently a substituent.
  • the substituent R 102 and the substituent R 103 are preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
  • the wavy line is a bond.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.
  • ring-forming carbon means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring.
  • Ring-forming atom means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).
  • the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (Protium), deuterium (Deuterium), and tritium (Tritium).
  • substituents include an aryl group, a heterocyclic group, an alkyl group (a linear or branched alkyl group, a cycloalkyl group, a haloalkyl group), and an aralkyl group as described above.
  • an aryl group, a heterocyclic group, an alkyl group, a halogen atom, an alkylsilyl group, an arylsilyl group, and a cyano group are preferable.
  • substituents are preferred. These substituents include alkenyl groups, alkynyl groups, alkoxy groups, aryloxy groups in addition to the aryl groups, heterocyclic groups, alkyl groups, aralkyl groups, alkylsilyl groups, arylsilyl groups, halogen atoms, and cyano groups described above. May be further substituted with groups, alkylthio groups, arylthio groups, siloxanyl groups, alkylamino groups, arylamino groups, amino groups, aldehyde groups, carbonyl groups, ester groups, carbamoyl groups, hydroxyl groups, nitro groups, and carboxy groups. . A plurality of these substituents may be bonded to each other to form a ring.
  • the alkenyl group having 2 to 30 carbon atoms may be linear, branched or cyclic, and examples thereof include a vinyl group, a propenyl group, a butenyl group, an oleyl group, an eicosapentaenyl group, and docosahexaenyl.
  • Group, styryl group, 2,2-diphenylvinyl group, 1,2,2-triphenylvinyl group, 2-phenyl-2-propenyl group, cyclopentadienyl group, cyclopentenyl group, cyclohexenyl group, and cyclohexadi An enyl group etc. are mentioned.
  • the alkynyl group having 2 to 30 carbon atoms may be linear, branched or cyclic, and examples thereof include ethynyl, propynyl and 2-phenylethynyl.
  • the alkoxy group having 1 to 30 carbon atoms is represented as —OZ a .
  • Z a include alkyl groups of 1 to 30 carbon atoms.
  • Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.
  • the alkoxy group preferably has 1 to 20 carbon atoms.
  • Examples of the halogenated alkoxy group in which the alkoxy group is substituted with a halogen atom include a group in which the alkoxy group having 1 to 30 carbon atoms is substituted with one or more fluorine atoms.
  • the aryloxy group having 6 to 30 ring carbon atoms is represented by —OZ b .
  • Zb include the aryl group having 6 to 30 ring carbon atoms.
  • the ring-forming carbon number of the aryloxy group is preferably 6-20.
  • Examples of the aryloxy group include a phenoxy group.
  • the alkylthio group having 1 to 30 carbon atoms is represented as —SR V.
  • RV include the alkyl group having 1 to 30 carbon atoms.
  • the alkylthio group preferably has 1 to 20 carbon atoms.
  • An arylthio group having 6 to 30 ring carbon atoms is represented by —SR W. Examples of R W, and an aryl group the ring-forming carbon atoms 6 to 30.
  • the ring-forming carbon number of the arylthio group is preferably 6-20.
  • the siloxanyl group is a silicon compound group via an ether bond, and examples thereof include a trimethylsiloxanyl group.
  • the alkylamino group having 2 to 30 carbon atoms is represented as —NHR V or —N (R V ) 2 .
  • Examples of RV include the alkyl group having 1 to 30 carbon atoms.
  • the arylamino group having 6 to 60 ring carbon atoms is represented by —NHR W or —N (R W ) 2 .
  • R W and an aryl group the ring-forming carbon atoms 6 to 30.
  • the aldehyde group, carbonyl group, ester group, carbamoyl group, and amino group may be substituted with an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, a heterocyclic ring, or the like.
  • the alicyclic hydrocarbon, aromatic hydrocarbon, and heterocyclic ring may further have a substituent.
  • unsubstituted in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the substituent.
  • carbon number XX to YY in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms in the case where the ZZ group is unsubstituted and substituted. In this case, the number of carbon atoms in the substituent is not included.
  • “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
  • atom number XX to YY in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted and substituted. The number of atoms of the substituent in the case is not included.
  • YY is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
  • the ring structure when substituents are bonded to each other to form a ring structure, the ring structure is a saturated ring, an unsaturated ring, an aromatic hydrocarbon ring, or a heterocyclic ring.
  • the aromatic hydrocarbon ring and the heterocyclic ring include a ring structure derived from the above-described monovalent group.
  • examples of the aromatic hydrocarbon group and the heterocyclic group in the linking group include divalent or higher groups obtained by removing one or more atoms from the above-described monovalent group.
  • the “chain or branched hydrocarbon group having 2 to 30 carbon atoms having a carbon-carbon double bond” in the linking group is a divalent group obtained by removing one or more atoms from the above alkenyl group.
  • the above-mentioned groups are mentioned, and the “chain or branched hydrocarbon group having 2 to 30 carbon atoms having a carbon-carbon triple bond” is obtained by removing one or more atoms from the alkynyl group described above.
  • a group having a valence higher than that is mentioned.
  • the organic EL element which concerns on one Embodiment of this invention can be used for electronic devices, such as a display apparatus and a light-emitting device.
  • the display device include display components such as an organic EL panel module, a television, a mobile phone, a tablet, and a personal computer.
  • the light emitting device include lighting and vehicle lamps.
  • a barrier layer may be provided adjacent to the anode side or cathode side of the light emitting layer.
  • the barrier layer is preferably disposed in contact with the light emitting layer and blocks at least one of holes, electrons, and excitons.
  • the barrier layer transports electrons, and the holes reach a layer (for example, an electron transport layer) on the cathode side of the barrier layer. Stop that.
  • an organic EL element contains an electron carrying layer, it is preferable to contain the said barrier layer between a light emitting layer and an electron carrying layer.
  • the barrier layer transports holes, and the electrons reach a layer on the anode side of the barrier layer (for example, a hole transport layer).
  • a layer on the anode side of the barrier layer for example, a hole transport layer.
  • the organic EL element includes a hole transport layer
  • a barrier layer may be provided adjacent to the light emitting layer so that excitation energy does not leak from the light emitting layer to the peripheral layer.
  • the excitons generated in the light emitting layer are prevented from moving to a layer (for example, an electron transport layer or a hole transport layer) closer to the electrode than the barrier layer.
  • the light emitting layer and the barrier layer are preferably joined.
  • the compound according to an embodiment of the present invention may be included in the hole transport layer, may be included in the electron transport layer, or is included in both the hole transport layer and the electron transport layer. May be.
  • the hole transport layer and the electron transport layer are formed by the above coating method using a solvent and a solution containing the compound according to an embodiment of the present invention. It is preferable to do.
  • compound A2 (4.14 g, 9.36 mmol), benzamidine hydrochloride (1.47 g, 9.36 mmol), EtOH 10 mL, and NaOH (0.450 g, 11.2 mmol) were added and heated to reflux for 5 hours.
  • the produced solid was collected by filtration and washed with ethanol to obtain a compound A3 (4.47 g, yield 88%) as a pyrimidine intermediate.
  • HPLC High Performance Liquid
  • Chromatography LC
  • LC-MS Liquid Chromatography-Mass Spectrometry
  • Example 1 (Washing the substrate) A glass substrate with an ITO transparent electrode of 25 mm ⁇ 25 mm ⁇ thickness 1.1 mm (manufactured by Geomatek Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 5 minutes.
  • CLEVIOUS AI4083 (trade name) manufactured by HERAEUS Co. was formed on the ITO substrate with a thickness of 30 nm by spin coating. After the film formation, unnecessary portions were removed with acetone, and then baked on a hot plate at 200 ° C. for 10 minutes in the atmosphere to prepare a base substrate on which a base layer was formed.
  • the compound H-1 obtained in Synthesis Example 1 was used as the host material, the compound D-1 was used as the dopant material, and the compound H-1: compound D-1 was mixed at a mixing ratio of 90:10.
  • a 6 mass% toluene solution was prepared. Ultrasound was used to dissolve the material. By visually observing this toluene solution, it was confirmed that all the compounds were completely dissolved and became transparent.
  • a coating film was formed on the base substrate by spin coating so as to have a film thickness of 50 nm. After the coating film formation, unnecessary portions were removed with toluene and dried by heating on a hot plate at 200 ° C. to prepare a coated laminated substrate having a light emitting layer formed thereon. Note that all operations for forming the light emitting layer were performed in a glove box in a nitrogen atmosphere.
  • Example 2 An organic EL device was produced in the same manner as in Example 1 except that Compound H-2 obtained in Synthesis Example 2 was used instead of Compound H-1 as the host material.
  • the obtained organic EL element was made to emit light by direct current drive, and the external quantum yield (EQE) at a current density of 10 mA / cm 2 was measured. The measurement results are shown in Table 1.
  • Example 1 An organic EL device was prepared in the same manner as in Example 1 except that the following comparative compound Ha was used as the host material instead of the compound H-1, but the material did not dissolve in the toluene solution. Since the solution was not cloudy and the solution could not be prepared, the device could not be produced.
  • Example 2 An organic EL device was prepared by the same method as in Example 1 except that the following comparative compound Hb was used instead of the compound H-1 as a host material. As a result, uniform light emission was not obtained.
  • Example 1 and Example 2 As described above, it was confirmed that the compound according to one embodiment of the present invention used in Example 1 and Example 2 was excellent in solubility and heat resistance. Moreover, as Table 1 showed, the organic EL element of Example 1 and Example 2 has confirmed that external quantum efficiency EQE was high.

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  • Engineering & Computer Science (AREA)
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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Devices For Indicating Variable Information By Combining Individual Elements (AREA)

Abstract

La présente invention concerne un composé qui comporte une première structure représentée par la formule générale (1) et une deuxième structure représentée par la formule générale (2), et qui peut comporter une troisième structure représentée par la formule générale (3), la première structure, la deuxième structure et la troisième structure étant chacune contenue de manière indépendante dans une molécule du composé. Le composé comporte également une quatrième structure partielle représentée par la formule générale (4), la quatrième structure partielle étant soit contenue à l'intérieur de la première structure, soit liée à au moins l'une de la première structure, de la deuxième structure ou de la troisième structure.
PCT/JP2016/054181 2015-02-13 2016-02-12 Composé, composition, élément organique électroluminescent, et dispositif électronique WO2016129687A1 (fr)

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