# US 2020/0403158 A1 · Organic electroluminescence device and compound for organic electroluminescence device

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- Number: US 2020/0403158 A1
- Document ID: US20200403158A1
- Status: Published application
- Kind: A1
- Application number: 16/809,480
- Filed: 2020-03-04
- Published: 2020-12-24
- Earliest claimed: 2019-06-21
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Akinori YAMATANI
- Web page: https://patentgrep.com/patent/US20200403158A1

## CPC

- C09K 11/06: containing organic luminescent materials
- C07F 7/0816: {said ring comprising Si as a ring atom}
- C07F 7/30: Germanium compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 85/658: {Organoboranes}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1037: with sulfur
- C09K 2211/104: with other heteroatoms
- C09K 2211/1092: containing sulfur as the only heteroatom
- C09K 2211/1096: containing other heteroatoms
- 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 includes a first electrode, a second electrode, and an emission layer between the first electrode and the second electrode, wherein the emission layer includes a compound represented by Formula 1 below. Embodiments of the present disclosure exhibit improved emission efficiency and long life characteristics:

## Claims

### Claim 1

An organic electroluminescence device, comprising:
a first electrode;
a second electrode on the first electrode; and
an emission layer 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 thereof, and
wherein the emission layer comprises a compound represented by Formula 1:
wherein in Formula 1,
M1 and M2 are each independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heterocycle of 2 to 30 carbon atoms to form a ring,
Ra is a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boryl group, a substituted or unsubstituted phosphinyl group, a substituted or unsubstituted phosphineoxy group, a substituted or unsubstituted phosphine sulfide group, a substituted or unsubstituted sulfonyl group, or a substituted or unsubstituted sulfinyl group,
Rb is a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, or a substituted or unsubstituted amino group,
Ra and/or Rb are optionally combined with M1 or M2 to form a ring, and
a substituent of M1 and M2 is a polycyclic hetero group represented by Formula 2:
wherein in Formula 2,
X is Si or Ge,
M3 and M4 are each independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heterocycle of 2 to 30 carbon atoms to form a ring,
L is a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms to form a ring, and
Rc and Rd are each independently a substituted or unsubstituted alkyl group of 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, or a substituted or unsubstituted amino group, or
Rc and Rd are combined with each other to form a substituted or unsubstituted hydrocarbon ring of 5 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heterocycle of 2 to 30 carbon atoms to form a ring.

### Claim 2 (depends on 1)

The organic electroluminescence device of claim 1, wherein Formula 1 is represented by Formula 1-1 or Formula 1-2:
wherein in Formula 1-2,
Y1 is B and Y2 is NRa, or Y1 is N and Y2 is BRb,
Z is a direct linkage, O, S, C═O, BRe, NRf, CRgRh, SiRiRj, GeRkRl, PORm, PSRn, SO, or SO2, and
Re to Rn are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring,
wherein in Formula 1-1 and Formula 1-2,
R11 to R18 and R21 to R31 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group, or are combined with an adjacent group to form a fused ring,
one of R11 to R18 or a substituent of the fused ring formed from R11 to R18 is the polycyclic hetero group represented by Formula 2,
one of R21 to R31 or a substituent of the fused ring formed from R21 to R31 is the polycyclic hetero group represented by Formula 2, and
Ra and Rb are the same as defined in Formula 1.

### Claim 3 (depends on 1)

The organic electroluminescence device of claim 1, wherein Formula 2 is represented by Formula 2-1 or Formula 2-2:
wherein in Formula 2-1 and Formula 2-2,
R41 to R48 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group, and
L, Rc, and Rd are the same as defined in Formula 2.

### Claim 4 (depends on 2)

The organic electroluminescence device of claim 2, wherein Formula 1-1 is represented by Formula 1-1A or Formula 1-1B:
wherein in Formula 1-1B, M5 is a substituted or unsubstituted hydrocarbon ring of 5 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heterocycle of 2 to 30 carbon atoms to form a ring, and
wherein in Formula 1-1A and Formula 1-1B, Ra and Rb are the same as defined in Formula 1, and X, L, M3, M4, Rc, and Rd are the same as defined in Formula 2.

### Claim 5 (depends on 2)

The organic electroluminescence device of claim 2, wherein Formula 1-2 is represented by one selected from Formulae 1-2A to 1-2C:
wherein in Formula 1-2C,
Q is a direct linkage, O, S, C═O, BRg, or NRh, and
Rg and Rh are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring,
wherein in Formula 1-2A to Formula 1-2C,
Ra, Rb, Y1, Y2, Z, and R21 to R31 are the same as defined in Formula 1-2.

### Claim 6 (depends on 2)

The organic electroluminescence device of claim 2, wherein Formula 1-2 is represented by one selected from Formula 1-2D to Formula 1-2F:
wherein in Formula 1-2F,
M6 is a substituted or unsubstituted hydrocarbon ring of 5 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heterocycle of 2 to 30 carbon atoms to form a ring, and
in Formula 1-2D to Formula 1-2F, R21 to R31, Y1, Y2, and Z are the same as defined in Formula 1-2, and X, L, M3, M4, Rc, and Rd are the same as defined in Formula 2.

### Claim 7 (depends on 1)

The organic electroluminescence device of claim 1, wherein the emission layer is to emit delayed fluorescence.

### Claim 8 (depends on 1)

The organic electroluminescence device of claim 1, wherein the emission layer is a delayed fluorescence emission layer comprising a host and a dopant, and
the dopant comprises the compound represented by Formula 1.

### Claim 9 (depends on 1)

The organic electroluminescence device of claim 1, wherein the emission layer is to emit blue light having a central wavelength of 430 nm to 490 nm.

### Claim 10 (depends on 1)

The organic electroluminescence device of claim 1, wherein the emission layer comprises at least one compound selected from Compound Group 1:

### Claim 11

A compound represented by Formula 1:
wherein in Formula 1,
M1 and M2 are each independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 carbon atoms, or a substituted or unsubstituted heterocycle of 2 to 30 carbon atoms,
Ra is a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boryl group, a substituted or unsubstituted phosphinyl group, a substituted or unsubstituted phosphineoxy group, a substituted or unsubstituted phosphine sulfide group, a substituted or unsubstituted sulfonyl group, or a substituted or unsubstituted sulfinyl group,
Rb is a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, or a substituted or unsubstituted amino group,
Ra and/or Rb are optionally combined with M1 or M2 to form a ring, and
a substituent of M1 and M2 is a polycyclic hetero group represented by Formula 2:
wherein in Formula 2,
X is Si or Ge,
M3 and M4 are each independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 carbon atoms, or a substituted or unsubstituted heterocycle of 2 to 30 carbon atoms,
L is a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms, and
Rc and Rd are each independently a substituted or unsubstituted alkyl group of 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, or a substituted or unsubstituted amino group, or
Rc and Rd are combined with each other to form a substituted or unsubstituted hydrocarbon ring of 5 to 30 carbon atoms, or a substituted or unsubstituted heterocycle of 2 to 30 carbon atoms.

### Claim 12 (depends on 11)

The compound of claim 11, wherein Formula 1 is represented by Formula 1-1 or Formula 1-2:
wherein in Formula 1-2,
Y1 is B and Y2 is NRa, or Y1 is N and Y2 is BRb,
Z is a direct linkage, O, S, C═O, BRe, NRf, CRgRh, SiRiRj, GeRkRl, PORm, PSRn, SO, or SO2, and
Re to Rn are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring,
wherein in Formula 1-1 and Formula 1-2,
R11 to R18 and R21 to R31 are each independently a substituent of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group, or are combined with an adjacent group to form a fused ring,
one of R11 to R18 or a substituent of the fused ring formed from R11 to R18 is the polycyclic hetero group represented by Formula 2,
one of R21 to R31 or a substituent of the fused ring formed from R21 to R31 is the polycyclic hetero group represented by Formula 2, and
Ra and Rb are the same as defined in Formula 1.

### Claim 13 (depends on 11)

The compound of claim 11, wherein Formula 2 is represented by Formula 2-1 or Formula 2-2:
wherein in Formula 2-1 and Formula 2-2,
R41 to R48 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group, and
L, Rc, and Rd are the same as defined in Formula 2.

### Claim 14 (depends on 12)

The compound of claim 12, wherein Formula 1-1 is represented by Formula 1-1A or Formula 1-1B:
wherein in Formula 1-1B, M5 is a substituted or unsubstituted hydrocarbon ring of 5 to 30 carbon atoms, or a substituted or unsubstituted heterocycle of 2 to 30 carbon atoms, and
wherein in Formula 1-1A and Formula 1-1B, Ra and Rb are the same as defined in Formula 1, and X, L, M3, M4, Rc, and Rd are the same as defined in Formula 2.

### Claim 15 (depends on 12)

The compound of claim 12, wherein Formula 1-2 is represented by one selected from Formulae 1-2A to 1-2C:
wherein in Formula 1-2C,
Q is a direct linkage, O, S, C═O, BRg, or NRh, and
Rg and Rh are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms to form a ring,
wherein in Formula 1-2A to Formula 1-2C,
Ra, Rb, Y1, Y2, Z, and R21 to R31 are the same as defined in Formula 1-2.

### Claim 16 (depends on 12)

The compound of claim 12, wherein Formula 1-2 is represented by one selected from Formula 1-2D to Formula 1-2F:
wherein in Formula 1-2F,
M6 is a substituted or unsubstituted hydrocarbon ring of 5 to 30 carbon atoms, or a substituted or unsubstituted heterocycle of 2 to 30 carbon atoms, and
in Formula 1-2D to Formula 1-2F, R21 to R31, Y1, Y2, and Z are the same as defined in Formula 1-2, and X, L, M3, M4, Rc, and Rd are the same as defined in Formula 2.

### Claim 17 (depends on 11)

The compound of claim 11, wherein M1 and M2 are each independently a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted dibenzothiophene ring.

### Claim 18 (depends on 11)

The compound of claim 11, wherein M3 and M4 are substituted or unsubstituted benzene rings.

### Claim 19 (depends on 11)

The compound of claim 11, wherein the compound represented by Formula 1 is a material to emit thermally activated delayed fluorescence.

### Claim 20 (depends on 11)

The compound of claim 11, wherein Formula 1 is at least one selected from Compound Group 1: