# US 2020/0403160 A1 · Organic electroluminescence device and fused polycyclic compound for organic electroluminescence device

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- Number: US 2020/0403160 A1
- Document ID: US20200403160A1
- Status: Published application
- Kind: A1
- Application number: 16/814,880
- Filed: 2020-03-10
- Published: 2020-12-24
- Earliest claimed: 2019-06-19
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Naoya SAKAMOTO
- Web page: https://patentgrep.com/patent/US20200403160A1

## CPC

- C09K 11/06: containing organic luminescent materials
- C07F 5/027: {Organoboranes and organoborohydrides}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/658: {Organoboranes}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1055: with other heteroatoms
- C09K 2211/1096: containing other heteroatoms
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/171: {Electron injection layers}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 2101/10: Triplet emission
- H10K 2101/20: Delayed fluorescence emission
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

An organic electroluminescence device of the embodiments includes oppositely disposed first electrode and second electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one among the organic layers includes a fused polycyclic compound represented by Formula 1 below, thereby showing improved emission efficiency and long life: Formula 1

## Claims

### Claim 1

An organic electroluminescence device, comprising:
a first electrode;
a second electrode facing the first electrode; and
a plurality of organic layers between the first electrode and the second electrode, wherein the first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, In, Sn, and Zn, a compound of two or more thereof, a mixture of two or more thereof, and an oxide of one or more thereof,
wherein at least one organic layer among the plurality of organic layers comprises a fused polycyclic compound, and
the fused polycyclic compound comprises:
a fused polycyclic heterocycle in which five rings are fused, the fused polycyclic heterocycle comprising one boron atom and two nitrogen atoms,
an amine group connected with one ring in the fused polycyclic heterocycle; and
a substituted or unsubstituted aromatic hydrocarbon ring which is connected with one or more rings, to which the amine group is not connected in the fused polycyclic heterocycle, via two heteroatoms which are each independently selected from the group consisting of a boron atom, an oxygen atom, a sulfur atom and a nitrogen atom.

### Claim 2 (depends on 1)

The organic electroluminescence device of claim 1, wherein
the plurality of organic layers comprises:
a hole transport region on the first electrode;
an emission layer on the hole transport region; and
an electron transport region on the emission layer, and
the emission layer comprises the fused polycyclic compound.

### Claim 3 (depends on 2)

The organic electroluminescence device of claim 2, wherein the emission layer is to emit delayed fluorescence.

### Claim 4 (depends on 2)

The organic electroluminescence device of claim 2, wherein
the emission layer is a delayed fluorescence emission layer comprising a host and a dopant, and
the dopant comprises the fused polycyclic compound.

### Claim 5 (depends on 1)

The organic electroluminescence device of claim 1, wherein
in the fused polycyclic heterocycle, the five rings are formed by connecting three substituted or unsubstituted benzene rings via one boron atom and two nitrogen atoms, and
the amine group and the boron atom are positioned para in one benzene ring among the three benzene rings.

### Claim 6 (depends on 1)

The organic electroluminescence device of claim 1, wherein the fused polycyclic compound is represented by Formula 1:
in Formula 1,
X1 and X2 are each independently BAr5, O, S, or NAr6,
Ar1 to Ar6 are each independently a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring,
Ar1 and Ar2 are optionally combined with each other to form a ring,
R1 to R4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R1 to R4 are optionally combined with an adjacent group to form a ring,
n1 and n2 are each independently an integer of 0 to 2, and
n3 and n4 are each independently an integer of 0 to 4.

### Claim 7 (depends on 6)

The organic electroluminescence device of claim 6, wherein the fused polycyclic compound represented by Formula 1 is represented by any one among Formula 2-1 to Formula 2-3:
in Formula 2-1 to Formula 2-3,
Y is CR7R8, O, or S,
R5 to R8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, where each of a plurality of R5 and R6 is optionally combined with an adjacent group to form a ring,
n5 and n6 are each independently an integer of 0 to 4, and
X1 and X2, R1 to R4, Ar3 and Ar4, and n1 to n4 are the same as defined in Formula 1.

### Claim 8 (depends on 6)

The organic electroluminescence device of claim 6, wherein the fused polycyclic compound represented by Formula 1 is represented by any one among Formula 3-1 to Formula 3-5:
in Formula 3-1 to Formula 3-5,
X11 and X21 are each independently O, S, or NAr6,
X12 and X22 are each independently BAr5, O, or S, and
R1 to R4, Ar1 to Ar6, and n1 to n4 are the same as defined in Formula 1.

### Claim 9 (depends on 6)

The organic electroluminescence device of claim 6, wherein Ar3 and Ar4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

### Claim 10 (depends on 6)

The organic electroluminescence device of claim 6, wherein R3 is a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, or a substituted or unsubstituted phenyl group, and each of a plurality of R3 groups is optionally combined with an adjacent group to form a ring.

### Claim 11 (depends on 6)

The organic electroluminescence device of claim 6, wherein R4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group.

### Claim 12 (depends on 1)

The organic electroluminescence device of claim 1, wherein the fused polycyclic compound is selected among compounds in Compound Group 1:

### Claim 13

An organic electroluminescence device, comprising:
a first electrode;
a second electrode facing the first electrode; and
a plurality of organic layers between the first electrode and the second electrode,
wherein at least one organic layer among the plurality of organic layers comprises a fused polycyclic compound represented by Formula 1:
in Formula 1,
X1 and X2 are each independently BAr5, O, S, or NAr6,
Ar1 to Ar6 are each independently a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring,
Ar1 and Ar2 are optionally combined with each other to form a ring,
R1 to R4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, or combined with an adjacent group to form a ring,
n1 and n2 are integers of 0 to 2, and
n3 and n4 are integers of 0 to 4.

### Claim 14

A fused polycyclic compound represented by the following Formula 1:
in Formula 1,
X1 and X2 are each independently BAr5, O, S, or NAr6,
Ar1 to Ar6 are each independently a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring,
Ar1 and Ar2 may be combined with each other to form a ring,
R1 to R4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, and any of R1 to R4 are optionally combined with an adjacent group to form a ring,
n1 and n2 are each independently an integer of 0 to 2, and
n3 and n4 are each independently an integer of 0 to 4.

### Claim 15 (depends on 14)

The fused polycyclic compound of claim 14, wherein the fused polycyclic compound represented by Formula 1 is represented by any one among Formula 2-1 to Formula 2-3:
in Formula 2-1 to Formula 2-3,
Y is CR7R8, O, or S,
R5 to R8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 60 carbon atoms to form a ring, where each of a plurality of R5 and R6 is optionally combined with an adjacent group to form a ring,
n5 and n6 are each independently an integer of 0 to 4, and
X1 and X2, R1 to R4, Ar3 and Ar4, and n1 to n4 are the same as defined in Formula 1.

### Claim 16 (depends on 14)

The fused polycyclic compound of claim 14, wherein the fused polycyclic compound represented by Formula 1 is represented by any one among Formula 3-1 to Formula 3-5:
in Formula 3-1 to Formula 3-5,
X11 and X21 are each independently O, S, or NAr6,
X12 and X22 are each independently BAr5, O, or S, and
R1 to R4, Ar1 to Ar6, and n1 to n4 are the same as defined in Formula 1.

### Claim 17 (depends on 14)

The fused polycyclic compound of claim 14, wherein Ar3 and Ar4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

### Claim 18 (depends on 14)

The fused polycyclic compound of claim 14, wherein R3 is a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, or a substituted or unsubstituted phenyl group, and each of a plurality of R3 groups is optionally combined with an adjacent group to form a ring.

### Claim 19 (depends on 14)

The fused polycyclic compound of claim 14, wherein R4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group.

### Claim 20 (depends on 14)

The fused polycyclic compound of claim 14, wherein the fused polycyclic compound is selected among compounds in Compound Group 1: