Use of dibenzofurans and dibenzothiophenes substituted by nitrogen-bonded five-membered heterocyclic rings in organic electronics
AssigneeBASF SE
InventorsNicolle Langer, Christian Schildknecht, Christian Lennartz, Gerhard Wagenblast, Thomas Schäfer
Life of this patent
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Abstract
The present invention relates to the use of dibenzofurans and dibenzothiophenes which have at least one nitrogen-bonded five-membered heterocyclic ring as a substituent as host, blocker and/or charge transport material in organic electronics. The present invention further relates to dibenzofurans and dibenzothiophenes which comprise at least one nitrogen-bonded five-membered heterocyclic ring and at least one carbazolyl radical as substituents, to a process for preparation thereof, and to the use of these compounds in organic electronics.
Claims49
An organic light-emitting diode, comprising:
- at least one compound of formula (I):
- wherein
- X is S or O;
- R1 and R2 are each independently aryl, heteroaryl, alkyl, cycloalkyl, heterocycloalkyl, a crosslinkable or polymerizable group bonded via a spacer, —NR3R4, —P(O)R5R6, —PR7R8, —S(O)2R9, —S(O)R10, —SR11 or —OR12, or a C group;
- R3, R4 are each independently aryl, heteroaryl, alkyl, cycloalkyl or heterocycloalkyl, a crosslinkable or polymerizable group bonded via a spacer,
- or
- R3 and R4 form, together with the nitrogen atom, a cyclic radical which has 3 to 10 ring atoms and may be unsubstituted or substituted by one or more substituents selected from alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl and a group with donor or acceptor action and/or may be fused to one or more further cyclic radicals having 3 to 10 ring atoms, wherein the fused radicals may be unsubstituted or substituted by one or more substituents selected from alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, a crosslinkable or polymerizable group bonded via a spacer, or a group with donor or acceptor action;
- R5, R6, R7, R8, R9, R10, R11 and R12 are each independently aryl,
- heteroaryl, alkyl, cycloalkyl or heterocycloalkyl, a crosslinkable or polymerizable group bonded via a spacer,
- n is 0, 1, 2, 3 or 4,
- m is 0, 1, 2 or 3,
- p is 1 or 2, wherein m+p is ≦4,
- C is a five-membered saturated or unsaturated heterocyclic radical of formula (II)
- wherein
- A1 is independently CRa, N or NRb;
- A2 is independently CRc, N or NRd;
- A3 is independently CRe, N or NRf;
- A4 is independently CRg, N or NRh
- Ra, Rb, Rc, Rd, Re, Rf, Rg and Rh are each independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, heterocycloalkyl, a crosslinkable or polymerizable group bonded via a spacer;
- or
- one combination of 2 R groups selected from the group consisting of
- (Ra or Rb) and (Rc or Rd),
- (Re or Rf) and (Rg or Rh), and
- (Rc or Rd) and (Re or Rf)
- may optionally form, together with the carbon or nitrogen atom, a cyclic radical which has 3 to 10 ring atoms and may be unsubstituted or substituted by one or more substituents selected from alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, a crosslinkable or polymerizable group bonded via a spacer, or a group with donor or acceptor action, and/or may be fused to one or more further cyclic radicals having 3 to 10 ring atoms, wherein the fused radicals may be unsubstituted or substituted by one or more substituents selected from alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, a crosslinkable or polymerizable group bonded via a spacer, or a group with donor or acceptor action;
- wherein the C group is bonded in the 2 and/or 4 position,
- or
- two units of the general formula (I) are bridged to one another via a bond, a linear or branched, saturated or unsaturated bridge optionally interrupted by at least one heteroatom or via O, wherein this bridge in the general formula (I) is bonded in place of Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh or via and/or in place of R1 or R2, in monomeric, polymerized or crosslinked form.
A compound of formula (III)
- wherein
- X is S or O;
- R2 are each independently aryl, heteroaryl, alkyl, cycloalkyl, heterocycloalkyl, a crosslinkable or polymerizable group bonded via a spacer, —NR3R4, —P(O)R5R6, —PR7R8, —S(O)2R9, —S(O)R10, —SR11 or —OR12,
- R3, R4 are each independently aryl, heteroaryl, alkyl, cycloalkyl or heterocycloalkyl, a crosslinkable or polymerizable group bonded via a spacer,
- or R3 and R4 form, together with the nitrogen atom, a cyclic radical which has 3 to 10 ring atoms and may be unsubstituted or substituted by one or more substituents selected from alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl and a group with donor or acceptor action and/or may be fused to one or more further cyclic radicals having 3 to 10 ring atoms, wherein the fused radicals may be unsubstituted or substituted by one or more substituents selected from alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, a crosslinkable or polymerizable group bonded via a spacer, and a group with donor or acceptor action;
- R5, R6, R7, R8, R9, R10, R11 and R12 are each independently aryl,
- heteroaryl, alkyl, cycloalkyl or heterocycloalkyl, a crosslinkable or
- polymerizable group bonded via a spacer,
- R13, R14 are each independently aryl, heteroaryl, alkyl, cycloalkyl, heterocycloalkyl, a crosslinkable or polymerizable group bonded via a spacer, —NR3R4, —P(O)R5R6, —PR7R8, —S(O)2R9, —S(O)R10, —SR11 or —OR12,
- m is 0, 1, 2 or 3,
- p is 1 or 2, wherein m+p is ≦4,
- q is 0, 1, 2, 3 or 4,
- r is 0,1, 2, 3 or 4,
- s is 1,2, 3 or 4,
- C is a five-membered saturated or unsaturated heterocyclic radical of formula (II)
- wherein
- A1 is independently CRa, N or NRb;
- A2 is independently CRc, N or NRd;
- A3 is independently CRe, N or NRf;
- A4 is independently CRg, N or NRh
- Ra, Rb, Rc, Rd, Re, Rf, Rg and Rh are each independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, heterocycloalkyl, a crosslinkable or polymerizable group bonded via a spacer;
- or
- one combination of 2R groups selected from the group consisting of
- (Ra or Rb) and (Rc or Rd),
- (Re or Rf) and (Rg or Rh), and
- (Rc or Rd) and (Re or Rf)
- may optionally form, together with the carbon or nitrogen atom, a cyclic radical which has 3 to 10 ring atoms and may be unsubstituted or substituted by one or more substituents selected from alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, a crosslinkable or polymerizable group bonded via a spacer, or a group with donor or acceptor action, and/or may be fused to one or more further cyclic radicals having 3 to 10 ring atoms, wherein the fused radicals may be unsubstituted or substituted by one or more substituents selected from alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, a crosslinkable or polymerizable group bonded via a spacer, or a group with donor or acceptor action;
- wherein the C group is bonded in the 2 and/or 4 position,
- or
- two units of the general formula (III) are bridged to one another via a bond, a linear or branched, saturated or unsaturated bridge optionally interrupted by at least one heteroatom or via O, wherein this bridge in the general formula (III) is bonded in place of Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, R13, R14 or via and/or in place of R2.
Dependencies are inferred from the claim text.