Organic electroluminescence device and electronic appliance using the same
地域：
Tokyo
摘要
An organic electroluminescence device, comprising: a cathode; an anode; and an emitting layer disposed between the cathode and the anode, wherein the emitting layer includes a compound represented by the following formula (1) and a compound represented by the following formula (11), provided that at least one of Ar101 and Ar102 is a monovalent group represented by the following formula (12).
說明書
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The present application claims priority under 37 U.S.C. § 371 to International Patent Application No. PCT/JP2019/031944, filed Aug. 14, 2019, which claims priority to and the benefit of Japanese Patent Application No. 2018-152971, filed on Aug. 15, 2018. The contents of these applications are hereby incorporated by reference in their entireties.
The invention relates to an organic electroluminescence device and an electronic appliance using the same.
When voltage is applied to an organic electroluminescence device (hereinafter, referred to as an organic EL device in several cases), holes and electrons are injected into an emitting layer from an anode and a cathode, respectively. Then, thus injected holes and electrons are recombined in the emitting layer, and excitons are formed therein.
Patent Documents 1 to 8 disclose that compounds having a specific fused ring structure are used as a dopant material of an emitting layer of an organic EL device.
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- [Patent Document 1] WO 2015/102118 A1
- [Patent Document 2] WO 2016/143624 A1
- [Patent Document 3] WO 2016/143819 A1
- [Patent Document 4] WO 2016/152544 A1
- [Patent Document 5] WO 2017/126443 A1
權(quán)利要求
The invention claimed is:1. An organic electroluminescence device, comprising:a cathode; an anode; and an emitting layer disposed between the cathode and the anode, wherein the emitting layer comprises a compound represented by the following formula (2) and a compound represented by the following formula (11): ![embedded image]()
wherein in the formula (2), R1A forms a substituted or unsubstituted heterocyclic ring by bonding with one or more selected from the group consisting of R11 and R21, or do not form a substituted or unsubstituted heterocyclic ring; R2A forms a substituted or unsubstituted heterocyclic ring by bonding with one or more selected from the group consisting of R13 and R14, or do not form a substituted or unsubstituted heterocyclic ring; R1A and R2A which do not form the substituted or unsubstituted heterocyclic ring are independently a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; one or more sets of adjacent two or more among R11 to R21 form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring; R11 to R21 which do not form the substituted or unsubstituted heterocyclic ring or the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, —Si(R901)(R902)(R903), —O—(R904), —S—(R905), —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; and R901 to R907 are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; when two or more of each of R901 to R907 are present, the two or more of each of R901 to R907 may be the same or different; ![embedded image]()
wherein in the formula (11), R101 to R108 is independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, —Si(R901)(R902)(R903), —O—(R904), —S—(R905), —N(R906)(R907), a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; adjacent two or more among R101 to R104, and adjacent two or more among R105 to R108 do not form a ring by bonding with each other; R901 to R907 are as defined in formula (2); L101 and L102 are independently a single bond, a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group including 5 to 30 ring atoms; at least one of Ar101 and Ar102 is a monovalent group represented by the following formula (12); Ar101 and Ar102 which are not the monovalent groups represented by the following formula (12) are a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; and when Ar101 and Ar102 are both the monovalent group represented by the following formula (12), Ar101 and Ar102 which are the monovalent groups represented by the following formula (12) may be the same as or different from each other: ![embedded image]()
wherein in the formula (12), R131 and R132 are independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms; R131 and R132 do not form a ring by bonding with each other; and one or more sets of adjacent two of R111 to R118 form an unsaturated ring represented by the following formula (20) by bonding with each other, or do not form the unsubstituted ring represented by the following formula (20): ![embedded image]()
wherein in the formula (20), “***” indicates a position bonding to adjacent two among R111 to R118; when one or more sets of adjacent two among R111 to R118 form the unsaturated ring represented by the formula (20) by bonding with each other, one of R111 to R118 which do not form the unsaturated ring represented by the formula (20) and R121 to R124 is a single bond bonding with L101 or L102; when two or more unsaturated rings represented by the formula (20) are formed, a plurality of each of R121 to R124 may be the same as or different from each other; when one or more sets of adjacent two among R111 to R118 do not form the unsaturated ring represented by the formula (20), one of R111 to R118 is a single bond bonding with L101 or L102; in the case when the unsaturated ring represented by the formula (20) is formed and in the case when the unsaturated ring represented by the formula (20) is not formed, one or more sets of adjacent two among R111 to R118 which do not form the unsaturated ring represented by the formula (20) and are not a single bond bonding with L101 or L102 form a substituted or unsubstituted, saturated or unsaturated ring other than the unsaturated ring represented by the formula (20) or do not form a substituted or unsubstituted, saturated or unsaturated ring; R111 to R118 which do not form the unsaturated ring represented by the formula (20), do not form a substituted or unsubstituted, saturated or unsaturated ring other than the unsaturated ring represented by the formula (20), and are not a single bond bonding with L101 or L102, and R121 to R124 which are not a single bond bonding with L101 or L102 are independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, —Si(R901)(R902)(R903), —O—(R904), —S—(R905), —N(R906)(R907), a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; and R901 to R907 are as defined in the formula (2). 2. The organic electroluminescence device according to claim 1 , wherein R1A and R2A in the formula (2) are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms. 3. The organic electroluminescence device according to claim 1 , wherein R1A and R2A in the formula (2) are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms. 4. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (2) is a compound represented by the following formula (3): ![embedded image]()
wherein in the formula (3), R31 forms a substituted or unsubstituted heterocyclic ring by bonding with R46, or does not form a substituted or unsubstituted heterocyclic ring; R33 forms a substituted or unsubstituted heterocyclic ring by bonding with R47, or does not form a substituted or unsubstituted heterocyclic ring; R34 forms a substituted or unsubstituted heterocyclic ring by bonding with R51, or does not form a substituted or unsubstituted heterocyclic ring; R41 forms a substituted or unsubstituted heterocyclic ring by bonding with R42, or does not form a substituted or unsubstituted heterocyclic ring; one or more sets of adjacent two or more among R31 to R51 form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring; R31 to R51 which do not form the substituted or unsubstituted heterocyclic ring or the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, —Si(R901)(R902)(R903), —O—(R904), —S—(R905), —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; and R901 to R907 are as defined in the formula (2). 5. The organic electroluminescence device according to claim 4 , wherein R31 to R51 in the formula (3) are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms. 6. The organic electroluminescence device according to claim 4 , wherein the compound represented by the formula (3) is a compound represented by the following formula (3A): ![embedded image]()
wherein in the formula (3A), R61 is a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; and R62 to R65 are independently a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms. 7. The organic electroluminescence device according to claim 4 , wherein the compound represented by the formula (3) is a compound represented by the following formula (3B): ![embedded image]()
wherein in the formula (3B), R71 and R72 are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, —N(R906)(R907), or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; R73 to R75 are independently a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, —N(R906) (R907), or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; and R906 and R907 are as defined in the formula (2). 8. The organic electroluminescence device according to claim 4 , wherein the compound represented by the formula (3) is a compound represented by the following formula (3C): ![embedded image]()
wherein in the formula (3C), R81 and R82 are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms; and R83 to R86 are independently a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms. 9. The organic electroluminescence device according to claim 1 , wherein one of Ar101 and Ar102 in the formula (11) is a monovalent group represented by the formula (12). 10. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (11) is a compound represented by the following formula (13): ![embedded image]()
wherein in the formula (13), R101 to R108, L101 and L102 are as defined in the formula (11); Ar102 is a monovalent group represented by the formula (12), a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; R131 and R132 are as defined in the formula (12); one of R112a to R114a is a single bond bonding with L101; one or more sets of adjacent two among R111a; R112a to R114a which are not a single bond bonding with L101; and R115a to R118a form an unsaturated ring represented by the formula (20) by bonding with each other, or do not form an unsaturated ring represented by the formula (20); R111a; R112a to R114a which are not a single bond bonding with L101 and do not form an unsaturated ring represented by the formula (20); and R115a to R118a which do not form an unsaturated ring represented by the formula (20) are independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, —Si(R901)(R902)(R903), —O—(R904), —S—(R905), —N(R906)(R907), a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; and R901 to R907 are as defined in the formula (2). 11. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (11) is a compound represented by the following formula (14): ![embedded image]()
wherein in the formula (14), R101 to R108, L101, L102, R111, R113 to R118, R131 and R132 are as defined in any of the formulas (11) and (12); and Ar102 is a monovalent group represented by the formula (12), a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms. 12. The organic electroluminescence device according to claim 1 , wherein one of Ar101 and Ar102 in the formula (11) is a monovalent group represented by the formula (12) and the other is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms. 13. The organic electroluminescence device according to claim 1 , wherein Ar101 or Ar102 in the formula (11) which is not a monovalent group represented by the formula (12) is selected from groups represented by each of the following formulas (a1) to (a4): ![embedded image]()
wherein in the formulas (a1) to (a4), “*” is a single bond bonding with L101 or L102; R120 is a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, —Si(R901)(R902)(R903), —O—(R904), —S—(R905), —N(R906)(R907), a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; R901 to R907 are as defined in the formula (2); m1 is an integer of 0 to 4; m2 is an integer of 0 to 5; m3 is an integer of 0 to 7; when each of m1 to m3 is 2 or more, a plurality of R120's may be the same as or different from each other; and when each of m1 to m3 is 2 or more, a plurality of adjacent R120's form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring. 14. The organic electroluminescence device according to claim 1 , wherein L101 and L102 in the formula (11) are independently a substituted or unsubstituted arylene group including 6 to 14 ring carbon atoms. 15. The organic electroluminescence device according to claim 1 , wherein R131 and R132 in the formula (12) are independently a substituted or unsubstituted alkyl group including 1 to 10 carbon atoms. 16. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (11) is a compound represented by the following formula (15): ![embedded image]()
wherein in the formula (15), R101 to R108 and L102 are as defined in the formula (11); Ar102 is a monovalent group represented by the formula (12), a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; and R111, R113 to R118, R131, and R132 are as defined in the formula (12). 17. The organic electroluminescence device according to claim 1 , wherein R101 to R108 in the formula (11) are hydrogen atoms. 18. The organic electroluminescence device according to claim 1 , wherein R111 to R118 in the formula (12) which are not a single bond bonding with L101 are hydrogen atoms. 19. The organic electroluminescence device according to claim 1 , wherein one set of R111 and R112, R112 and R113, R113 and R114, R115 and R116, R116 and R117, and R117 and R118 in the formula (12) forms a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other. 20. The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (11) is a compound represented by the following formula (18): ![embedded image]()
wherein in the formula (18), L101a and L102a are independently a single bond, or a substituted or unsubstituted arylene group including 6 to 10 ring carbon atoms; Ar102a is a substituted or unsubstituted aryl group including 6 to 10 ring carbon atoms; and R131a and R132a are independently a hydrogen atom, a substituted or unsubstituted aryl group including 1 to 18 ring carbon atoms, or a substituted or unsubstituted alkyl group including 1 to 10 carbon atoms. 21. The organic electroluminescence device according to claim 1 , further comprising a hole-transporting layer between the anode and the emitting layer. 22. The organic electroluminescence device according to claim 1 , further comprising an electron-transporting layer between the cathode and the emitting layer. 23. An electronic appliance provided with the organic electroluminescence device according to claim 1 .
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