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US 12,398,148 B2Granted
Polycyclic compound and organic electroluminescence device including the same
AssigneeSamsung Display Co., Ltd.
InventorAkinori Yamatani
Life of this patent
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Abstract
Disclosed are a polycyclic compound and an organic electroluminescence device including the same. The polycyclic compound according to an embodiment is represented by the following Formula 1, wherein in Formula 1, Cy1 to Cy3, L1 to L4, and m are as respectively defined in the detailed description of the current disclosure.
Claims21
A polycyclic compound represented by the following Formula 1:
- where L1 to L4 are each independently a substituted or unsubstituted divalent alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted divalent amino group, a substituted or unsubstituted divalent oxy group, a substituted or unsubstituted divalent thio group, a substituted or unsubstituted divalent sulfoxy group, a substituted or unsubstituted divalent phosphine oxide group, or a substituted or unsubstituted divalent silyl group,
- m is 0 or 1, and
- Cy1 to Cy3 are each independently represented by the following Formula 2-1 or 2-2, where one of Cy1 or Cy2 is represented by the following Formula 2-2:
- where X is one of O, S, or NY1,
- R1 and R2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted sulfoxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted silyl group,
- Y1 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted boron group, a substituted or unsubstituted sulfoxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted carbonyl group, or a substituted or unsubstituted silyl group,
- n1 is an integer of 0 to 4, and
- n2 is an integer of 0 to 2,
- 1) wherein when m is 1, n2 is 0, one of L1 and L2 is a substituted divalent amino group, one of L3 and L4 is a substituted divalent amino group, Cy2 is represented by Formula 2-2, and Cy1 and Cy3 are each represented by Formula 2-1,
- an other one of L1 and L2 and/or an other one of L3 and L4 is a substituted or unsubstituted divalent amino group, a substituted or unsubstituted divalent oxy group, a substituted or unsubstituted divalent thio group, a substituted or unsubstituted divalent sulfoxy group, a substituted or unsubstituted divalent phosphine oxide group, or a substituted or unsubstituted divalent silbyl group,
- 2) wherein when m is 0,
- i) at least one selected from L1 and L2 is a divalent methyl group substituted with an unsubstituted phenyl group, or a divalent silyl group substituted with a phenyl group,
- ii) when one of L1 and L2 is the divalent methyl group, and when an other one of L1 and L2 is NY1,
- Y1 does not join with an adjacent group to form a ring,
- iii) when L1 and L2 are each a divalent methyl group,
- L1 and L2 are each substituted with two unsubstituted phenyl groups, and
- iv) when one of L1 and L2 is a divalent methyl group and an other one of L1 and L2 is a divalent silyl group,
- the divalent methyl group and the divalent silyl group are each substituted with two unsubstituted phenyl groups,
- 3) wherein when m is O and Cy1 and Cy2 are each represented by Formula 2-2,
- i) X of Cy1 or Cy2 is O or NY1, and
- ii) when one of L1 and L2 is a divalent methyl group and an other one of L1 and L2 is a substituted or unsubstituted divalent amino group,
- the divalent methyl group is substituted with two unsubstituted phenyl groups,
- 4) wherein when m is 1, n1 is 1, one of L1 and L2 is a divalent thio group, one of L3 and L4 is a divalent thio group, Cy2 is represented by Formula 2-2, n2 is O, X is S, and Cy1 and Cy3 are each represented by Formula 2-1,
- another one of L1 and L2 and/or another one of L3 and L4 is a divalent alkyl group having 1 to 10 carbon atoms and substituted with a substituted or unsubstituted aryl group having 6 to 15 carbon atoms for forming a ring, a divalent amino group substituted with a substituted or unsubstituted aryl group having 6 to 15 carbon atoms for forming a ring, or a divalent silyl group substituted with a substituted or unsubstituted aryl group having 6 to 15 carbon atoms for forming a ring, and
- 5) wherein when m is 1, Cy1 and Cy3 are each independently represented by the Formula 2-2, Cy2 is represented by Formula 2-1, X is NY1, and L1 to L4 are each a substituted divalent methyl group,
- the substituted divalent methyl group is a methyl group substituted with two unsubstituted phenyl groups.
23 more elements
An organic electroluminescence device, comprising:
- a first electrode;
- a hole transport region provided on the first electrode;
- an emission layer provided on the hole transport region;
- an electron transport region provided on the emission layer;
- and
- a second electrode provided on the electron transport region,
- wherein the hole transport region comprises a polycyclic compound represented by the following Formula 1:
- where L1 to L4 are each independently a substituted or unsubstituted divalent alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted divalent amino group, a substituted or unsubstituted divalent oxy group, a substituted or unsubstituted divalent thio group, a substituted or unsubstituted divalent sulfoxy group, a substituted or unsubstituted divalent phosphine oxide group, or a substituted or unsubstituted divalent silyl group,
- m is 0 or 1, and
- Cy1 to Cy3 are each independently represented by the following Formula 2-1 or 2-2, where one of Cy1 or Cy2 is represented by the following Formula 2-2:
- where X is one of O, S, or NY1,
- R1 and R2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted sulfoxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted silyl group,
- Y1 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted boron group, a substituted or unsubstituted sulfoxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted carbonyl group, or a substituted or unsubstituted silyl group,
- n1 is an integer of 0 to 4, and
- n2 is an integer of 0 to 2,
- wherein when m is 1, n2 is 0, one of L1 and L2 is a substituted divalent amino group, one of L3 and L4 is a substituted divalent amino group, Cy2 is represented by Formula 2-2, and Cy1 and Cy3 are each represented by Formula 2-1,
- an other one of L1 and L2 and/or an other one of L3 and L4 is a substituted or unsubstituted divalent amino group, a substituted or unsubstituted divalent oxy group, a substituted or unsubstituted divalent thio group, a substituted or unsubstituted divalent sulfoxy group, a substituted or unsubstituted divalent phosphine oxide group, or a substituted or unsubstituted divalent silyl group, and wherein when m is 0,
- i) at least one selected from L1 and L2 is a divalent methyl group substituted with an unsubstituted phenyl group, or a divalent silyl group substituted with a phenyl group, and
- ii) when one of L1 and L2 is the divalent methyl group, and when an other one of L1 and L2 is NY1,
- Y1 does not join with an adjacent group to form a ring, wherein when m is 0 and Cy1 and Cy2 are each represented by Formula 2-2,
- X of Cy1 or Cy2 is O or NY1, and
- wherein when m is 1, n1 is 1, one of L1 and L2 is a divalent thio group, one of L3 and L4 is a divalent thio group, Cy2 is represented by Formula -2, n2 is 0, X is S, and Cy1 and Cy3 are each represented by Formula 2-1,
- an other one of L1 and L2 and/or an other one of L3 and L4 is a divalent alkyl group having 1 to 10 carbon atoms and substituted with a substituted or unsubstituted aryl group having 6 to 15 carbon atoms for forming a ring, a divalent amino group substituted with a substituted or unsubstituted aryl group having 6 to 15 carbon atoms for forming a ring, or a divalent silyl group substituted with a substituted or unsubstituted aryl group having 6 to 15 carbon atoms for forming a ring.
20 more elements
A polycyclic compound represented by the following Formula 3-1:
- where X1 is one of O, S, or NY1,
- R3 and R4 are each independently a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted sulfoxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted silyl group,
- n3 to n4 are each independently an integer of 0 to 4, and
- L1 to L4 are each independently a substituted or unsubstituted divalent alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted divalent silyl group, a substituted or unsubstituted divalent oxy group, or a substituted or unsubstituted divalent thio group,
- Y1 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted boron group, a substituted or unsubstituted sulfoxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted carbonyl group, or a substituted or unsubstituted silyl group,
- wherein when n3 and n4 are each 1, one of L1 and L2 is a divalent thio group, one of L3 and L4 is a divalent thio group, and X1 is S,
- another one of L1 and L2 and/or another one of L3 and L4 is a divalent alkyl group having 1 to 10 carbon atoms and substituted with a substituted or unsubstituted aryl group having 6 to 15 carbon atoms for forming a ring, or a divalent silyl group substituted with a substituted or unsubstituted aryl group having 6 to 15 carbon atoms for forming a ring.
4 more elements
A display device comprising an organic electroluminescence device,
- wherein the organic electroluminescence device comprises:
- a first electrode;
- a hole transport region provided on the first electrode;
- an emission layer provided on the hole transport region;
- an electron transport region provided on the emission layer;
- and
- a second electrode provided on the electron transport region,
- wherein the hole transport region comprises a polycyclic compound represented by the following Formula 1:
- where L1 to L4 are each independently a substituted or unsubstituted divalent alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted divalent amino group, a substituted or unsubstituted divalent oxy group, a substituted or unsubstituted divalent thio group, a substituted or unsubstituted divalent sulfoxy group, a substituted or unsubstituted divalent phosphine oxide group, or a substituted or unsubstituted divalent silyl group,
- m is 0 or 1, and
- Cy1 to Cy3 are each independently represented by the following Formula 2-1 or 2-2, where one of Cy1 or Cy2 is represented by the following Formula 2-2:
- where X is one of O, S, or NY1,
- R1 and R2 are each independently a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted sulfoxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted silyl group,
- Y1 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted boron group, a substituted or unsubstituted sulfoxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted carbonyl group, or a substituted or unsubstituted silyl group,
- n1 is an integer of 0 to 4, and
- n2 is an integer of 0 to 2,
- wherein when m is 1, n2 is 0, one of L1 and L2 is a substituted divalent amino group, one of L3 and L4 is a substituted divalent amino group, Cy2 is represented by Formula 2-2, and Cy1 and Cy3 are each represented by Formula 2-1,
- an other one of L1 and L2 and/or an other one of L3 and L4 is a substituted or unsubstituted divalent amino group, a substituted or unsubstituted divalent oxy group, a substituted or unsubstituted divalent thio group, a substituted or unsubstituted divalent sulfoxy group, a substituted or unsubstituted divalent phosphine oxide group, or a substituted or unsubstituted divalent silyl group, and wherein when m is 0,
- i) at least one selected from L1 and L2 is a divalent methyl group substituted with an unsubstituted phenyl group, or a divalent silyl group substituted with a phenyl group, and
- ii) when one of L1 and L2 is the divalent methyl group, and when an other one of L1 and L2 is NY1,
- Y1 does not join with an adjacent group to form a ring,
- wherein when m is 0 and Cy1 and Cy2 are each represented by Formula 2-2,
- X of Cy1 or Cy2 is O or NY1, and
- wherein when m is 1, n1 is 1, one of L1 and L2 is a divalent thio group, one of L3 and L4 is a divalent thio group, Cy2 is represented by Formula 2-2, n2 is 0, X is S, and Cy1 and Cy3 are each represented by Formula 2-1,
- an other one of L1 and L2 and/or an other one of L3 and L4 is a divalent alkyl group having 1 to 10 carbon atoms and substituted with a substituted or unsubstituted aryl group having 6 to 15 carbon atoms for forming a ring, a divalent amino group substituted with a substituted or unsubstituted aryl group having 6 to 15 carbon atoms for forming a ring, or a divalent silyl group substituted with a substituted or unsubstituted aryl group having 6 to 15 carbon atoms for forming a ring.
22 more elements
Dependencies are inferred from the claim text.