# US 11,299,459 B2 · Compound for organic electric element, organic electric element comprising the same and electronic device thereof

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- Number: US 11,299,459 B2
- Document ID: US11299459B2
- Status: Granted
- Kind: B2
- Application number: 15/753,803
- Filed: 2016-08-04
- Published: 2018-10-04
- Granted: 2022-04-12
- Earliest claimed: 2015-08-20
- Assignees: Duk San Neolux Co., Ltd.
- Applicants: Duk San Neolux Co., Ltd.
- Inventors: Soung Yun Mun; Seul-gi Kim; Sun-Hee Lee; Yeon Hee Choi; Jung Wook Lee
- Web page: https://patentgrep.com/patent/US11299459B2

## CPC

- C07D 209/94: containing carbocyclic rings other than six-membered
- C07D 209/82: Carbazoles; Hydrogenated carbazoles
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 333/76: Dibenzothiophenes
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/10: linked by a carbon chain containing aromatic rings
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 405/14: containing three or more hetero rings
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 409/14: containing three or more hetero rings
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 491/048: the oxygen-containing ring being five-membered
- C07D 495/04: Ortho-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07F 7/00: Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F 7/0816: {said ring comprising Si as a ring atom}
- C09B 57/00: Other synthetic dyes of known constitution
- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/00: Organic materials used in the body or electrodes of devices covered by this subclass
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1088: containing oxygen as the only heteroatom
- H10K 50/15: Hole transporting layers
- H10K 85/624: {containing six or more rings}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present invention provides the compound represented by Formula 1, and an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises the compound represented by Formula 1. The driving voltage of an organic electronic device can be lowered, and the luminous efficiency, color purity and life time of an organic electronic device can be improved by comprising the compound represented by Formula 1 in the organic material layer.

## Claims

### Claim 1

A compound of Formula 4 or 5:
wherein:
X and Y are each O or S,
R1 to R12 are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a fused ring group of a C6-C60 aromatic ring and a C3-C60 aliphatic ring, a C1-C50 alkyl group, a C2-C20 alkenyl group, a C1-C50 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxyl group, and -L′—N(Ra)(Rb), and neighboring groups of R1 to R12 are optionally linked to each other to form a ring, wherein L′ is selected from the group consisting of a single bond; a C1-C60 arylene group; a fluorenylene group; a C2-C60 heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a fused ring of a C3-C60 aliphatic ring and a C6-C60 aromatic ring, and L′ may be further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a C7-C20 arylalkyl group, a C8-C20 arylalkenyl group and -N(Ra)(Rb),Ra and Rb are each independently selected from the group consisting of a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a fused ring of a C3-C60 aliphatic ring and a C6-C60 aromatic ring,
L1 is selected from the group consisting of a single bond; a C6-C60 arylene group; a fluorenylene group; a C2-C60 heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P; a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring, and
the moiety
is represented by one of Formulas Z-3 to Z-10 and Z-15 to Z-22:
in Formulas Z-3 to Z10 and Z15 to Z-22:
W1 and W2 are each independently a single bond, C(R13)(R14), N(Ar2), O or S,
Ar2 and Ar3 is selected from the group consisting of a C6-C60 aryl group, a fluorenyl group, a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring, a C2-C60 heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P, and -L′-N(Ra)(Rb), and
R13 and R14 are each independently selected from the group consisting of hydrogen, deuterium, a C1-C50) alkyl group, a C2-C30 alkenyl group, a C2-C30 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxyl group, a C1-C30 silyl group, a C6-C60 aryl group, a C2-C60 heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a fluorenyl group, a fused ring group of a C6-C60 aromatic ring and a C3-C60 aliphatic ring, and -L′-N(Ra)(Rb), and R13 and R14 is optionally linked to each other to form a spiro-compound together with C to which R13 and R14 are bond.

### Claim 2 (depends on 1)

The compound of claim 1, wherein L′ is selected from the group of the following Formulas:
in the Formulas,
R21 to R23 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a C7-C20 arylalkyl group, a C8-C20 arylalkenyl group, and —N(Ra)(Rb), wherein Ra and Rb are the same as defined in claim 1,
b1 is an integer of 0 to 4, b2 is an integer of 0 to 6, b3 is an integer of 0 to 5, b4 is an integer of 0 to 8, and when b1 to b4 are each an integer of 2 or more, neighboring R21 to neighboring R23 are optionally linked to each other to form a ring, and
A is N(Ar2), O, S, C(R13)(R14) or Si(R13)(R14), wherein Ar2 is the same as Ar2 defined in claim 1 and R13 and R14 are the same as defined in claim 1.

### Claim 3 (depends on 1)

An organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises the compound of claim 1.

### Claim 4 (depends on 3)

The organic electric element of claim 3, wherein the compound is comprised in at least one layer of a hole injection layer, a hole transport layer, an emission-auxiliary layer and a light emitting layer.

### Claim 5 (depends on 4)

The organic electric element of claim 4, wherein the compound is used as phosphorescent host material of the light emitting layer.

### Claim 6 (depends on 4)

The organic electric element of claim 4, wherein the compound is used as red phosphorescent host material of the light emitting layer.

### Claim 7 (depends on 3)

The organic electric element of claim 3, further comprising a layer for improving luminous efficiency formed on one side of the first electrode and/or one side of the second electrode, the side facing the organic material layer.

### Claim 8 (depends on 3)

The organic electric element of claim 3, wherein the organic material layer is formed by one of the processes of spin coating, nozzle printing, inkjet printing, slot coating, dip coating and roll-to-roll.

### Claim 9 (depends on 3)

An electronic device comprising a display device and a control unit for driving the display device, wherein the display device comprises the organic electric element of claim 3.

### Claim 10 (depends on 9)

The electronic device of claim 9, wherein the organic electric element is an organic light emitting diode, an organic solar cell, an organic photo conductor, an organic transistor, or an element for monochromatic or white illumination.

### Claim 11

A compound represented by Formula 6:
wherein:
a1 and a2 are each an integer of 0 or 1 and a1+a2=1, and p1 and p2 are each an integer of 0 to 4,
Ar1 is selected from the group consisting of a C6-C60 aryl group, a fluorenyl group, a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring, a C2-C60 heterocyclic group including at least one heteroatom of O, N, S, Si or P, and -L′-N(Ra)(Rb),
X and Y are each independently O, S, C(R13)(R14), wherein R13 and R14 are each independently selected from the group consisting of hydrogen, deuterium, a C1-C50 alkyl group, a C2-C30 alkenyl group, a C2-C30 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxyl group, a C1-C30 silyl group, a C6-C60 aryl group, a C2-C60 heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a fluorenyl group, a fused ring group of a C6-C60 aromatic ring and a C3-C60 aliphatic ring, and -L′-N(Ra)(Rb), and R13 and R14 is optionally linked to each other to form a spiro-compound together with C or Si to which R13 and R14 are bond,
m and n are each an integer of 0 or 1, and m+n is an integer of 1 or 2,
R23, R24 and R25 are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a fused ring group of a C6-C60 aromatic ring and a C3-C60 aliphatic ring, a C1-C50 alkyl group, a C2-C20 alkenyl group, a C1-C50 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxyl group, and -L′-N(Ra)(Rb), and neighboring groups of R23, R24 and R25 are optionally linked to each other to form a ring,
L1 is selected from the group consisting of a single bond; a C6-C60 arylene group; a fluorenylene group; a C2-C60 heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P; a fused ring formed by a C6-C60 aromatic ring and a C3-C60 aliphatic ring,
L′ is selected from the group consisting of a single bond; a C6-C60 arylene group; a fluorenylene group; a C2-C60 heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a fused ring of a C3-C60 aliphatic ring and a C6-C60 aromatic ring, and L′ may be further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a C7-C20 arylalkyl group, a C8-C20 arylalkenyl group and —N(Ra)(Rb), Ra and Rb are each independently selected from the group consisting of a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a fused ring of a C3-C60 aliphatic ring and a C6-C60 aromatic ring, and
where R23 to R25, L1, Ar1, Ra and Rb are each an aryl group, a fluorenyl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxy group, an arylene group or a fluorenylene group, they may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a C7-C20 arylalkyl group and a C8-C20 arylalkenyl group.

### Claim 12 (depends on 11)

An organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises the compound of claim 11.

### Claim 13 (depends on 12)

An electronic device comprising a display device and a control unit for driving the display device, wherein the display device comprises the organic electric element of claim 12.

### Claim 14

A compound selected from the group consisting of the following compounds:

### Claim 15 (depends on 14)

An organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises the compound of claim 14.

### Claim 16 (depends on 15)

An electronic device comprising a display device and a control unit for driving the display device, wherein the display device comprises the organic electric element of claim 15.