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US 12,643,849 B2Granted
Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
AssigneeIdemitsu Kosan Co., Ltd.
InventorsYusuke Takahashi, Tasuku Haketa, Shota Tanaka, Hirokatsu Ito, Yu Kudo
Life of this patent
Estimating the term…
Abstract
A compound may improve the capability of an organic EL device, and an organic electroluminescent device including such compound may have improved capability and may be included in electronic devices. Such compounds may be of formula (1A) or formula (1B) (wherein the symbols are as defined in the description) organic electroluminescent device(s) may contain such compound(s), and electronic device(s) may include such organic electroluminescent device(s).
Claims14
A compound represented by the following formula (1A):
- in the formula (1A),
- N* is a central nitrogen atom,
- p represents 0 or 1,
- q represents 0 or 1,
- provided that p+q≥1,
- when p is 0 and q is 1, *a bonds to the nitrogen atom N*, and one selected from R6 to R10 is a single bond bonding to *b,
- when p is 1 and q is 0, one selected from R1 to R5 is a single bond bonding to *b,
- when p is 1 and q is 1, one selected from R1 to R5 is a single bond bonding to *a, and one selected from R6 to R10 is a single bond bonding to *b,
- R1 to R5 that are not a single bond bonding to *a or *b, R6 to R10 that are not a single bond bonding to *b, R11 to R14, and R21 to R27 each independently represent
- 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 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 aryloxy 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 substituent(s) 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, and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
- adjacent two selected from R1 to R5 that are not a single bond, adjacent two selected from R6 to R10 that are not a single bond, adjacent two selected from R11 to R14 that are not a single bond, and adjacent two selected from R21 to R27 do not bond to each other and therefore do not form a cyclic structure,
- provided that one or more pairs of two benzene rings bonding to each other selected from the benzene ring U, the benzene ring V and the benzene ring W may be crosslinked with CRxRy to form a substituted or unsubstituted fluorene structure, or may not be crosslinked and may not form a fluorene structure,
- Rx and Ry each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and Rx and Ry may bond via a single bond,
- Ar1 and Ar2 each are independently represented by any of the following formulae (1-a) to (1-e):
- in the formula (1-a),
- R31 to R35, R41 to R46, and R51 to R55 each independently represent
- 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 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 aryloxy 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 substituent(s) 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, and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
- provided that,
- one selected from R31 to R35 is a single bond bonding to *c,
- one selected from R41 to R46 is a single bond bonding to *d, and the other one selected from R41 to R46 is a single bond bonding to *e,
- ** is a bonding position to the nitrogen atom N*,
- m1 represents 0 or 1, and n1 represents 0 or 1,
- when m1 is 0 and n1 is 0, *e bonds to the nitrogen atom N*
- when m1 is 0 and n1 is 1, *c bonds to the nitrogen atom N*,
- when m1 is 1 and n1 is 0, one selected from R31 to R35 is a single bond bonding to *e,
- k represents 1 or 2,
- adjacent two selected from R31 to R35 that are not a single bond, adjacent two selected from R41 to R46 that are not a single bond, and adjacent two selected from R51 to R55 do not bond to each other and therefore do not form a cyclic structure,
- the benzene ring A and the benzene ring B, the benzene ring A and the benzene ring C, and the benzene ring B and the benzene ring C do not crosslink;
- in the formula (1-b),
- R61 to R68 each independently represent
- 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 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 aryloxy 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 substituent(s) 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, and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
- provided that, one selected from R61 to R68 is a single bond bonding to *f,
- ** represents a bonding position to the nitrogen atom N*,
- adjacent two selected from R61 to R68 that are not a single bond do not bond to each other and therefore do not form a cyclic structure;
- in the formula (1-c),
- R31 to R35, R41 to R46, **, *c, *d, and *e are the same as above,
- R71 to R80 each independently represent
- 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 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 aryloxy 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 substituent(s) 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, and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
- provided that, one selected from R71 to R80 is a single bond bonding to *h,
- m2 represents 0 or 1, n2 represents 0 or 1,
- when m2 is 0 and n2 is 0, *e bonds to the nitrogen atom N*,
- when m2 is 0 and n2 is 1, *c bonds to the nitrogen atom N*,
- when m2 is 1 and n2 is 0, one selected from R31 to R35 is a single bond bonding to *e,
- adjacent two selected from R31 to R35 that are not a single bond, adjacent two selected from R41 to R46 that are not a single bond, and adjacent two selected from R71 to R80 do not bond to each other and therefore do not form a cyclic structure,
- the benzene ring A and the benzene ring B do not crosslink;
- in the formula (1-d),
- R31 to R35, R41 to R46, **, *c, *d, and *e are the same as above,
- R81 to R92 each independently represent
- 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 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 aryloxy 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 substituent(s) 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, and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
- provided that, one selected from R81 to R92 is a single bond bonding to *g,
- m3 represents 0 or 1, n3 represents 0 or 1,
- when m3 is 0 and n3 is 0, *e bonds to the nitrogen atom N*,
- when m3 is 0 and n3 is 1, *c bonds to the nitrogen atom N*,
- when m3 is 1 and n3 is 0, one selected from R31 to R35 is a single bond bonding to *e,
- adjacent two selected from R31 to R35 that are not a single bond, adjacent two selected from R41 to R46 that are not a single bond, and adjacent two selected from R81 to R92 do not bond to each other and therefore do not form a cyclic structure,
- the benzene ring A and the benzene ring B do not crosslink;
- in the formula (1-e),
- R31 to R35, **, and *c are the same as above,
- R101 to R108 each independently represent
- 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 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 aryloxy 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 substituent(s) 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, and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
- provided that, one selected from R101 to R108 is a single bond bonding to *i,
- m4 represents 0 or 1,
- one of Ra and Rb is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or 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,
- adjacent two selected from R101 to R104 and R105 to R108 that are not a single bond do not bond to each other and therefore do not form a cyclic structure,
- provided that when Ar1 is represented by the formula (1-e), m4 is 1, and when Ar2 is represented by the formula (1-e), m4 is 0 or 1,
- ** represents a bonding position to the nitrogen atom N*,
- wherein, when either one of Ar1 or Ar2 has formula (1-b), (1-c), or (1-d), the other of Ar1 and Ar2 has formula (1-a), and
- wherein, when Ar1 or Ar2 has formula (1-e), m4 is 1.
113 more elements
Dependencies are inferred from the claim text.