Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
AssigneeIdemitsu Kosan Co., Ltd.
InventorsTasuku HAKETA, Takuto FUKAMI, Shota TANAKA, Yusuke TAKAHASHI, Tsukasa SAWATO
Life of this patent
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Abstract
Provided are a compound that further improves the performance of an organic EL element, an organic electroluminescent element having further improved element performance, and an electronic device including the organic electroluminescent element. A compound represented by the following formula (1): wherein each of the symbols in the formula (1) is defined in the description; an organic electroluminescent element including the compound; and an electronic device including the organic electroluminescent element.
Claims29
1:
- A compound represented by formula (1):
- wherein,
- N* is a central nitrogen atom,
- one of R1 and R2 is a single bond bonded to *a, and the other is a hydrogen atom,
- one of R3 and R4 is a single bond bonded to *b, and the other is a hydrogen atom,
- L1 is a single bond or a phenylene group,
- Ar is represented by any one of the following formulas (1-a) to (1-d):
- in the formula (1-a),
- ** represents a bonding position to the central nitrogen atom N*,
- m1 is 0 or 1, n1 is 0, 1 or 2,
- m1+n1 is 1, 2, or 3,
- R11 to R15 each are independently
- a hydrogen atom, a halogen atom, a nitro group, a cyano group,
- a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
- a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
- a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
- a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
- a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
- a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
- a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
- a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
- a mono-, di- or tri-substituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
- R21 to R26 and R31 to R35 each are independently
- a hydrogen atom, a halogen atom, a nitro group, a cyano group,
- a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
- a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
- a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
- a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
- a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
- a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms,
- a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
- a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
- a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
- a mono-, di- or tri-substituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
- provided that
- when m1 is 1 and n1 is 0, one selected from R11 to R15 is a single bond that is bonded to *c, and one selected from R21 to R26 is a single bond that is bonded to *d,
- when m1 is 0 and n1 is 1, one selected from R11 to R15 is a single bond that is bonded to *e,
- when m1 is 1 and n1 is 1, one selected from R11 to R15 is a single bond that is bonded to *c, one selected from R21 to R26 is a single bond that is bonded to *d, and another one selected from R21 to R26 is a single bond that is bonded to *e,
- when m1 is 0 and n1 is 2, two selected from R11 to R are single bonds that are bonded to *e,
- when m1 is 1 and n1 is 2, one selected from R11 to R15 is a single bond that is bonded to *c, one selected from R21 to R26 is a single bond that is bonded to *d, and other two selected from R21 to R26 are single bonds that are bonded to *e,
- R11 to R15 that are not the single bonds, R21 to R26 that are not the single bonds, and R31 to R35 that are not the single bonds are not bonded to each other and therefore do not form a ring structure,
- when R2 is a single bond that is bonded to *a, and m1 and n1 are 1, to any one of R21 to R26 that are single bonds bonded to *d, the other one of R21 to R26 located adjacent on a benzene ring is a single bond bonded to *e;
- in the formula (1-b),
- ** represents a bonding position to the central nitrogen atom N*,
- L2 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group;
- when R2 is a single bond that is bonded to *a, in the substituted or unsubstituted biphenylene group represented by L2, (i) with respect to a bonding position to the central nitrogen atom N* on one benzene ring, the other benzene ring is bonded at an ortho position or a meta position, or (ii) with respect to a bonding position to the central nitrogen atom N* on one benzene ring, the other benzene ring is bonded at a para position, and with respect to the bonding position to the one benzene ring on the other benzene ring, one of R41 to R48 that are single bonds is bonded at the ortho position or the meta position,
- one selected from R41 to R48 is a single bond that is bonded to *f, and R41 to R48 that are not the single bonds each are independently
- a hydrogen atom, a halogen atom, a nitro group, a cyano group,
- a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
- a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
- a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
- a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
- a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
- a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms,
- a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
- a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
- a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
- a mono-, di- or tri-substituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
- provided that R41 to R48 that are not the single bonds, and each substituent when L2 has a substituent are respectively not bonded to each other and therefore do not form a ring structure;
- in the formula (1-c),
- ** represents a bonding position to the central nitrogen atom N*,
- L3 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group,
- one selected from R51 to R60 is a single bond that is bonded to *g, and R51 to R60 that are not the single bonds each are independently
- a hydrogen atom, a halogen atom, a nitro group, a cyano group,
- a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
- a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
- a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
- a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
- a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
- a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms,
- a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
- a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
- a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
- a mono-, di- or tri-substituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
- provided that R51 to R60 that are not the single bonds, and each substituent when L3 has a substituent are respectively not bonded to each other and therefore do not form a ring structure;
- and
- in the formula (1-d),
- ** represents a bonding position to the central nitrogen atom N*,
- L4 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group,
- X is an oxygen atom, a sulfur atom, or CRaRb,
- Ra and Rb each are independently a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
- one selected from R61 to R68 is a single bond that is bonded to *h, and R61 to R68 that are not the single bond each are independently
- a hydrogen atom, a halogen atom, a nitro group, a cyano group,
- a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
- a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
- a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
- a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
- a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
- a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
- a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
- a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
- a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
- a mono-, di- or tri-substituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
- provided that R61 to R68 that are not the single bonds, and each substituent when L4 has a substituent are respectively not bonded to each other and therefore do not form a ring structure.
2:
- The compound according to claim 1, represented by the following formula (1-1) or (1-2),
- wherein in the formulas (1-1) and (1-2), N*, L1, and Ar are as defined in the formula (1).
3:
- The compound according to claim 1, represented by the following formula (1-3) or (1-4),
- wherein in the formulas (1-3) and (1-4), N*, L1, and Ar are as defined in the formula (1).
4:
- The compound according to claim 1, represented by the following formula (1-1-1) or (1-2-1),
- wherein in the formulas (1-1-1) and (1-2-1), N* and Ar are as defined in the formula (1).
5:
- The compound according to claim 1, represented by the following formula (1-1-2) or (1-2-2),
- wherein in the formulas (1-1-2) and (1-2-2), N* and Ar are as defined in the formula (1).
6:
- The compound according to claim 1, represented by the following formula (1-3-1) or (1-4-1),
- wherein in the formulas (1-3-1) and (1-4-1), N* and Ar are as defined in the formula (1).
7:
- The compound according to claim 1, represented by the following formula (1-3-2) or (1-4-2),
- wherein in the formulas (1-3-2) and (1-4-2), N* and Ar are as defined in the formula (1).
8:
- The compound according to claim 1, represented by the following formula (1-1a), (1-1b), (1-1c), or (1-1d),
- wherein in the formulas (1-1a), (1-1b), (1-1c), and (1-1d), N*, L1, L2, L3, L4, *c, *d, *e, *f, * g, *h, m1, n1, R11 to R15, R21 to R26, R31 to R35, R41 to R48, R51 to R60, R61 to R68, and X are as defined in the formula (1).
9:
- The compound according to claim 1, represented by the following formula (1-2a), (1-2b), (1-2c), or (1-2d),
- wherein in the formulas (1-2a), (1-2b), (1-2c), and (1-2d), N*, L1, L2, L3, L4, *c, *d, *e, *f, * g, *h, m1, n1, R11 to R15, R21 to R26, R31 to R35, R41 to R48, R1 to R60, R61 to R68, and X are as defined in the formula (1).
10:
- The compound according to claim 1, represented by the following formula (1-3a), (1-3b), (1-3c), or (1-3d),
- wherein in the formulas (1-3a), (1-3b), (1-3c), and (1-3d), N*, L1, L2, L3, L4, *C, *d, *e, *f, * g, *h, m1, n1, R11 to R15, R21 to R26, R31 to R35, R41 to R48, R1 to R60, R61 to R68, and X are as defined in the formula (1).
11:
- The compound according to claim 1, represented by the following formula (1-4a), (1-4b), (1-4c), or (1-4d),
- wherein in the formulas (1-4a), (1-4b), (1-4c), and (1-4d), N*, L1, L2, L3, L4, *C, *d, *e, *f, *g, *h, m1, n1, R11 to R15, R21 to R26, R31 to R35, R41 to R48, R51 to R60, R61 to R68, and X are as defined in the formula (1).
12:
- The compound according to claim 1, wherein the L2, L3 and L4 are each independently a single bond, an unsubstituted phenylene group or an unsubstituted biphenylene group.
13:
- The compound according to claim 1, wherein substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms represented by R11 to R15, R21 to R26, R31 to R35, R41 to R48, R51 to R60, R61 to R68, Ra and Rb each are independently selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group.
14:
- The compound according to claim 1, wherein substituted or unsubstituted aryl groups having 6 to 14 ring carbon atoms represented by R21 to R26, R31 to R35, R41 to R48, and R51 to R60 each are independently selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a phenanthryl group.
15:
- The compound according to claim 1, wherein Ar is represented by the formula (1-d), X is CRaRb, and both Ra and Rb are substituted or unsubstituted phenyl groups, or both Ra and Rb are methyl groups, or both Ra and Rb are substituted or unsubstituted phenyl groups, and Ra and Rb form a ring together.
(canceled)
17:
- The compound according to claim 1, wherein all of R21 to R26 that are not single bonds bonded to *d and that are not single bonds bonded to *e are hydrogen atoms.
18-21. (canceled)
22:
- The compound according to claim 1, formed of Compound 1, Compound 2, Compound 3, Compound 4, Compound 5, Compound 6, Compound 7, or Compound 8 below.
23:
- The compound according to claim 1, wherein the compound represented by the formula (1) contains at least one deuterium atom.
24:
- A material for organic electroluminescent elements, comprising:
- the compound according to claim 1.
25:
- An organic electroluminescent element, comprising:
- a cathode,
- an anode, and
- organic layers intervening between the cathode and the anode, the organic layers including a light emitting layer, at least one layer of the organic layers containing the compound according to claim 1.
26:
- The organic electroluminescent element according to claim 25, wherein the organic layers include a hole transporting zone intervening between the anode and the light emitting layer, and the hole transporting zone contains the compound.
27:
- The organic electroluminescent element according to claim 26, wherein the hole transporting zone includes a first hole transporting layer on an anode side and a second hole transporting layer on a cathode side, and the first hole transporting layer, the second hole transporting layer, or both of the first hole transporting layer and the second hole transporting layer contain the compound.
28:
- The organic electroluminescent element according to claim 27, wherein the second hole transporting layer contains the compound.
29:
- The organic electroluminescent element according to claim 27, wherein the second hole transporting layer is adjacent to the light emitting layer.
30:
- The organic electroluminescent element according to claim 25, wherein the light emitting layer contains a fluorescent dopant material.
31:
- The organic electroluminescent element according to claim 25, wherein the light emitting layer contains a phosphorescent dopant material.
32:
- An electronic device, comprising:
- the organic electroluminescent element according to claim 25.
Dependencies are inferred from the claim text.