# US 10,483,488 B2 · Organic light-emitting element

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- Number: US 10,483,488 B2
- Document ID: US10483488B2
- Status: Granted
- Kind: B2
- Application number: 15/108,149
- Filed: 2014-12-18
- Published: 2017-01-19
- Granted: 2019-11-19
- Earliest claimed: 2013-12-26
- Assignees: Toray Industries, Inc.
- Applicants: Toray Industries, Inc.
- Inventors: Guangnan Jin; Peng Wang; Fangrong Xu; Lingzhi Zhong; Takeshi Ishigaki; Daisaku Tanaka; Takeshi Ikeda; Takuya Nishiyama
- Web page: https://patentgrep.com/patent/US10483488B2

## CPC

- H10K 50/858: comprising refractive means, e.g. lenses
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- 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 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- G02F 1/133602: {Direct backlight}
- H10K 50/818: Reflective anodes, e.g. ITO combined with thick metallic layers
- H10K 50/82: Cathodes
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/653: {comprising only oxygen as heteroatom}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/655: {comprising only sulfur as heteroatom}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS

## Abstract

An organic light-emitting element, including a substrate, a first electrode, a light-emitting layer containing one organic or more layer film, and a light-emitting element of a second electrode are disclosed. The light-emitting element is provided with a covering layer. For the organic material contained in covering layer, at least one point in the wavelength range between 430 nm and 460 nm the attenuation coefficient is greater than 0.10 while in the wavelength range of 460 nm to 500 nm its attenuation coefficient is 0.10 or below. The organic light-emitting element achieves high light-emitting efficiency and color reproducibility, and can be used as organic EL display, backlight source for liquid crystal display, illumination, light source for measurement devices, indication board or identification lamp etc.

## Claims

### Claim 1

An organic light-emitting element, comprising a substrate, a first electrode, one layer or more of organic film including a light-emitting layer, and a second electrode element; the light-emitting element comprising a covering layer; the covering layer containing an organic material; at least one point in the wavelength range between 430 nm and 460 nm the attenuation coefficient being greater than 0.10 while in the wavelength range of 460 nm to 500 nm its attenuation coefficient being 0.10 or below.

### Claim 2 (depends on 1)

The organic light-emitting element of claim 1, wherein at least one point in the wavelength range between 430 nm and 460 nm its attenuation coefficient is greater than 0.12 while in the wavelength range of 460 nm to 500 nm its attenuation coefficient is 0.10 or below.

### Claim 3 (depends on 1)

The organic light-emitting element of claim 1, wherein the organic material contained in the covering layer is one or more compounds that have thiophene-based structure, furan-based structure or pyrrole-based structure.

### Claim 4 (depends on 3)

The organic light-emitting element of claim 3, wherein the compound having thiophene-based structure, furan-based structure or pyrrole-based structure is as expressed in Formula (1):
where, X is selected from a sulfur atom, an oxygen atom and N—R; and R is selected from hydrogen, deuterium, substitutable alkyl, substitutable cycloalkyl, substitutable heterocyclyl, substitutable alkenyl, substitutable cycloalkenyl, substitutable alkynyl, substitutable alkoxy, substitutable alkylthio, substitutable arylether, substitutable arylsulfide, substitutable aryl, substitutable heteroaryl, substitutable carbonyl, substitutable carboxyl, substitutable oxycarbonyl, substitutable carbamoyl, substitutable alkylamino and substitutable silyl;
where, R1 to R4 are identical or different, and each of R1 to R4 is independently selected from hydrogen, deuterium, halogen, substitutable alkyl, substitutable cycloalkyl, substitutable heterocyclyl, substitutable alkenyl, substitutable cycloalkenyl, substitutable alkynyl, substitutable alkoxy, substitutable alkylthio, substitutable arylether, substitutable arylsulfide, substitutable aryl, substitutable heteroaryl, substitutable cyano, substitutable carbonyl, substitutable carboxyl, substitutable oxycarbonyl, substitutable carbamoyl, substitutable alkylamino and substitutable silyl, and are optionally bonded with an adjacent substituent to form a ring;
wherein when substitution is made, the substituents are independently one or more selected from deuterium, halogen, C1-C15 alkyl, C3-C15 cycloalkyl, C3-C15 heterocyclyl, C2-C15 alkenyl, C4-C15 cycloalkenyl, C2-C15 alkynyl, C1-C15 alkoxy, C1-C15 alkylthio, C6-C55 arylether, C6-C55 arylsulfide, C6-C55 aryl, C5-C55 aromatic heterocyclyl, carbonyl, carboxyl, oxycarbonyl, carbamoyl, C1-C40 alkylamino and C3-C15 silyl that has 1 to 5 silicon atoms.

### Claim 5 (depends on 3)

The organic light-emitting element of claim 3, wherein the compound having thiophene-based structure, furan-based structure or pyrrole-based structure is as expressed in Formula (2):
where, X is selected from a sulfur atom, an oxygen atom and N—R; and R is selected from hydrogen, deuterium, substitutable alkyl, substitutable cycloalkyl, substitutable heterocyclyl, substitutable alkenyl, substitutable cycloalkenyl, substitutable alkynyl, substitutable alkoxy, substitutable alkylthio, substitutable arylether, substitutable arylsulfide, substitutable aryl, substitutable heteroaryl, substitutable carbonyl, substitutable carboxyl, substitutable oxycarbonyl, substitutable carbamoyl, substitutable alkylamino and substitutable silyl;
where, R1 to R4 are identical or different, and each of R1 to R4 is independently selected from hydrogen, deuterium, halogen, substitutable alkyl, substitutable cycloalkyl, substitutable heterocyclyl, substitutable alkenyl, substitutable cycloalkenyl, substitutable alkynyl, substitutable alkoxy, substitutable alkylthio, substitutable arylether, substitutable arylsulfide, substitutable aryl, substitutable heteroaryl, substitutable carbonyl, substitutable carboxyl, substitutable oxycarbonyl, substitutable carbamoyl, substitutable alkylamino and substitutable silyl, and are optionally bonded with an adjacent substituent to form a ring;
L1 is selected from arylene and heteroarylene, and forms a single bond with one or more of R1 to R4; and
R5 and R6 are identical or different, and each of R5 and R6 is independently selected from substitutable alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl, and n1 is an integer of 1 to 4, and at least one of R1 to R4 forms a bond with L1;
wherein when substitution is made, the substituents are independently one or more selected from deuterium, halogen, C1-C15 alkyl, C3-C15 cycloalkyl, C3-C15 heterocyclyl, C2-C15 alkenyl, C4-C15 cycloalkenyl, C2-C15 alkynyl, C1-C15 alkoxy, C1-C15 alkylthio, C6-C55 arylether, C6-C55 arylsulfide, C6-C55 aryl, C5-C55 aromatic heterocyclyl, carbonyl, carboxyl, oxycarbonyl, carbamoyl, C1-C40 alkylamino, and C3-C15 silyl that has 1 to 5 silicon atoms.

### Claim 6 (depends on 5)

The organic light-emitting element of claim 5, wherein n1 is 1 or 2.

### Claim 7 (depends on 6)

The organic light-emitting element of claim 6, wherein the compound having thiophene-based structure, furan-based structure or pyrrole-based structure is as expressed in Formula (3):
where, X is selected from a sulfur atom, an oxygen atom and N—R; and R is selected from hydrogen, deuterium, substitutable alkyl, substitutable cycloalkyl, substitutable heterocyclyl, substitutable alkenyl, substitutable cycloalkenyl, substitutable alkynyl, substitutable alkoxy, substitutable alkylthio, substitutable arylether, substitutable arylsulfide, substitutable aryl, substitutable heteroaryl, substitutable carbonyl, substitutable carboxyl, substitutable oxycarbonyl, substitutable carbamoyl, substitutable alkylamino and substitutable silyl;
where, R7 and R8 are identical or different, and each of R7 and R8 is independently selected from hydrogen, deuterium, halogen, substitutable alkyl, substitutable cycloalkyl, substitutable heterocyclyl, substitutable alkenyl, substitutable cycloalkenyl, substitutable alkynyl, substitutable alkoxy, substitutable alkylthio, substitutable arylether, substitutable arylsulfide, substitutable aryl, substitutable heteroaryl, substitutable cyano, substitutable carbonyl, substitutable carboxyl, substitutable oxycarbonyl, substitutable carbamoyl, substitutable alkylamino and substitutable silyl, and are optionally bonded with an adjacent substituent to form a ring;
each of L2 and L3 is selected from arylene and heteroarylene; and
each of R9 to R12 is selected from substitutable alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl;
wherein when substitution is made, the substituents are independently one or more selected from deuterium, halogen, C1-C15 alkyl, C3-C15 cycloalkyl, C3-C15 heterocyclyl, C2-C15 alkenyl, C4-C15 cycloalkenyl, C2-C15 alkynyl, C1-C15 alkoxy, C1-C15 alkylthio, C6-C55 arylether, C6-C55 arylsulfide, C6-C55 aryl, C5-C55 aromatic heterocyclyl, carbonyl, carboxyl, oxycarbonyl, carbamoyl, C1-C40 alkylamino, and C3-C15 silyl that has 1 to 5 silicon atoms.

### Claim 8 (depends on 1)

The organic light-emitting element of claim 1, wherein the covering layer contains a compound having pyrene-based structure.

### Claim 9 (depends on 8)

The organic light-emitting element of claim 8, wherein the compound having pyrene-based structure is as expressed in Formula (4):
where, R13 to R22 are identical or different, and each of R13 to R22 is independently selected from hydrogen, deuterium, halogen, substitutable alkyl, substitutable cycloalkyl, substitutable heterocyclyl, substitutable alkenyl, substitutable cycloalkenyl, substitutable alkynyl, substitutable alkoxy, substitutable alkylthio, substitutable arylether, substitutable arylsulfide, substitutable aryl, substitutable heteroaryl, substitutable cyano, substitutable carbonyl, substitutable carboxyl, substitutable oxycarbonyl, substitutable carbamoyl, substitutable alkylamino and substitutable silyl, and are optionally bonded with an adjacent substituent to form a ring;
wherein when substitution is made, the substituents are independently one or more selected from deuterium, halogen, C1-C15 alkyl, C3-C15 cycloalkyl, C3-C15 heterocyclyl, C2-C15 alkenyl, C4-C15 cycloalkenyl, C2-C15 alkynyl, C1-C15 alkoxy, C1-C15 alkylthio, C6-C55 arylether, C6-C55 arylsulfide, C6-C55 aryl, C5-C55 aromatic heterocyclyl, carbonyl, carboxyl, oxycarbonyl, carbamoyl, C1-C40 alkylamino, and C3-C15 silyl that has 1 to 5 silicon atoms.

### Claim 10 (depends on 9)

The organic light-emitting element of claim 9, wherein the compound having pyrene-based structure is as expressed in Formula (5):
where at least one of R13 to R22 is heteroaryl or aryl substituted with heteroaryl; where, R13 to R22 are identical or different, and each of R13 to R22 is independently selected from hydrogen, deuterium, halogen, substitutable alkyl, substitutable cycloalkyl, substitutable heterocyclyl, substitutable alkenyl, substitutable cycloalkenyl, substitutable alkynyl, substitutable alkoxy, substitutable alkylthio, substitutable arylether, substitutable arylsulfide, substitutable aryl, substitutable heteroaryl, substitutable cyano, substitutable carbonyl, substitutable carboxyl, substitutable oxycarbonyl, substitutable carbamoyl, substitutable alkylamino and substitutable silyl, and are optionally bonded with an adjacent substituent to form a ring;
L4 is selected from arylene and heteroarylene, and forms single bonds with one or more of R13 to R22; and
R23 and R24 are identical or different, and each of R23 and R24 is independently selected from substitutable alkyl, substitutable cycloalkyl, substitutable aryl, substitutable heteroaryl and substitutable heterocyclyl, and n2 is an integer of 1-4, and at least one of R13 to R22 forms a bond with L4;
wherein when substitution is made, the substituents are independently one or more selected from deuterium, halogen, C1-C15 alkyl, 15 C3-C15 cycloalkyl, C3-C15 heterocyclyl, C2-C15 alkenyl, C4-C15 cycloalkenyl, C2-C15 alkynyl, C1-C15 alkoxy, C1-C15 alkylthio, C6-C55 arylether, C6-C55 arylsulfide, C6-C55 aryl, C5-C55 aromatic heterocyclyl, carbonyl, carboxyl, oxycarbonyl, carbamoyl, C1-C40 alkylamino, and C3-C15 silyl that has 1 to 5 silicon atoms.

### Claim 11 (depends on 10)

The organic light-emitting element of claim 10, wherein n2 is 1 or 2.

### Claim 12 (depends on 11)

The organic light-emitting element of claim 11, wherein the compound having pyrene-based structure is as expressed in Formula (6):
where, R25 to R32 are identical or different, each of R25 to R32 is and are independently selected from hydrogen, deuterium, halogen, substitutable alkyl, substitutable cycloalkyl, substitutable heterocyclyl, substitutable alkenyl, substitutable cycloalkenyl, substitutable alkynyl, substitutable alkoxy, substitutable alkylthio, substitutable arylether, substitutable arylsulfide, substitutable aryl, substitutable heteroaryl, substitutable cyano, substitutable carbonyl, substitutable carboxyl, substitutable oxycarbonyl, substitutable carbamoyl, substitutable alkylamino and substitutable silyl, and are optionally bonded with an adjacent substituent to form a ring;
each of L5 and L6 is independently selected from arylene and heteroarylene; and
R33 to R36 are identical or different, and each of R33 to R36 is independently selected from substitutable alkyl, substitutable cycloalkyl, substitutable aryl, substitutable heteroaryl or substitutable heterocyclyl;
wherein when substitution is made, the substituents are independently one or more selected from deuterium, halogen, C1-C15 alkyl, C3-C15 cycloalkyl, C3-C15 heterocyclyl, C2-C15 alkenyl, C4-C15 cycloalkenyl, C2-C15 alkynyl, C1-C15 alkoxy, C1-C15 alkylthio, C6-C55 arylether, C6-C55 arylsulfide, C6-C55 aryl, C5-C55 aromatic heterocyclyl, carbonyl, carboxyl, oxycarbonyl, carbamoyl, C1-C40 alkylamino, and C3-C15 silyl that has 1 to 5 silicon atoms.

### Claim 13 (depends on 1)

The organic light-emitting element of claim 1, wherein the covering layer contains a compound having anthracene-based structure.

### Claim 14 (depends on 13)

The organic light-emitting element of claim 13, wherein the compound having anthracene-based structure is as expressed in Formula (7):
where, R37 to R46 are identical or different, and each of R37 to R46 is independently selected from hydrogen, deuterium, halogen, substitutable alkyl, substitutable cycloalkyl, substitutable heterocyclyl, substitutable alkenyl, substitutable cycloalkenyl, substitutable alkynyl, substitutable alkoxy, substitutable alkylthio, substitutable arylether, substitutable arylsulfide, substitutable aryl, substitutable heteroaryl, substitutable cyano, substitutable carbonyl, substitutable carboxyl, substitutable oxycarbonyl, substitutable carbamoyl, substitutable alkylamino and substitutable silyl, and are optionally bonded with an adjacent substituent to form a ring;
when substitution is made, the substituents are independently one or more selected from deuterium, halogen, C1-C15 alkyl, C3-C15 cycloalkyl, C3-C15 heterocyclyl, C2-C15 alkenyl, C4-C15 cycloalkenyl, C2-C15 alkynyl, C1-C15 alkoxy, C1-C15 alkylthio, C6-C55 arylether, C6-C55 arylsulfide, C6-C55 aryl, C5-C55 aromatic heterocyclyl, carbonyl, carboxyl, oxycarbonyl, carbamoyl, C1-C40 alkylamino, and C3-C15 silyl that has 1 to 5 silicon atoms.

### Claim 15 (depends on 14)

The organic light-emitting element of claim 14, wherein the compound having anthracene-based structure is as expressed in Formula (8):
where, R47 to R56 are identical or different, and each of R47 to R56 is independently selected from hydrogen, deuterium, halogen, substitutable alkyl, substitutable cycloalkyl, substitutable heterocyclyl, substitutable alkenyl, substitutable cycloalkenyl, substitutable alkynyl, substitutable alkoxy, substitutable alkylthio, substitutable arylether, substitutable arylsulfide, substitutable aryl, substitutable heteroaryl, substitutable cyano, substitutable carbonyl, substitutable carboxyl, substitutable oxycarbonyl, substitutable carbamoyl, substitutable alkylamino and substitutable silyl, and are optionally bonded with an adjacent substituent to form a ring;
L7 is selected from arylene and heteroarylene, and forms single bonds with one or more of R47 to R56;
R57 and R58 are identical or different, and each of R57 and R58 is independently selected from substitutable alkyl, substitutable cycloalkyl, substitutable aryl, substitutable heteroaryl and substitutable heterocyclyl, and n3 is an integer of 1-4, and at least one of R47-R56 forms a bond with L7;
wherein when substitution is made, the substituents are independently one or more selected from deuterium, halogen, C1-C15 alkyl, C3-C15 cycloalkyl, C3-C15 heterocyclyl, C2-C15 alkenyl, C4-C15 cycloalkenyl, C2-C15 alkynyl, C1-C15 alkoxy, C1-C15 alkylthio, C6-C55 arylether, C6-C55 arylsulfide, C6-C55 aryl, C5-C55 aromatic heterocyclyl, carbonyl, carboxyl, oxycarbonyl, carbamoyl, C1-C40 alkylamino, and C3-C15 silyl that has 1 to 5 silicon atoms.

### Claim 16 (depends on 15)

The organic light-emitting element of claim 15, wherein n3 is 1 or 2.

### Claim 17 (depends on 16)

The organic light-emitting element of claim 16, wherein the compound having anthracene-based structure is as expressed in Formula (9):
where, R59 to R66 are identical or different, and each of R59 to R66 is independently selected from hydrogen, deuterium, halogen, substitutable alkyl, substitutable cycloalkyl, substitutable heterocyclyl, substitutable alkenyl, substitutable cycloalkenyl, substitutable alkynyl, substitutable alkoxy, substitutable alkylthio, substitutable arylether, substitutable arylsulfide, substitutable aryl, substitutable heteroaryl, substitutable cyano, substitutable carbonyl, substitutable carboxyl, substitutable oxycarbonyl, substitutable carbamoyl, substitutable alkylamino and substitutable silyl, and are optionally bonded with an adjacent substituent to form a ring;
each of L8 and L9 is independently selected from arylene and heteroarylene; and
R67 to R70 are identical or different, and each of R67 to R70 is independently selected from substitutable alkyl, substitutable cycloalkyl, substitutable aryl, substitutable heteroaryl and substitutable heterocyclyl;
wherein when substitution is made, the substituents are independently one or more selected from deuterium, halogen, C1-C15 alkyl, C3-C15 cycloalkyl, C3-C15 heterocyclyl, C2-C15 alkenyl, C4-C15 cycloalkenyl, C2-C15 alkynyl, C1-C15 alkoxy, C1-C15 alkylthio, C6-C55 arylether, C6-C55 arylsulfide, C6-C55 aryl, C5-C55 aromatic heterocyclyl, carbonyl, carboxyl, oxycarbonyl, carbamoyl, C1-C40 alkylamino, and C3-C15 silyl that has 1 to 5 silicon atoms.