# US 2014/0191207 A1 · Silicon-based compound and organic light emitting diode comprising the same

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- Number: US 2014/0191207 A1
- Document ID: US20140191207A1
- Status: Published application
- Kind: A1
- Application number: 13/949,170
- Filed: 2013-07-23
- Published: 2014-07-10
- Earliest claimed: 2013-01-04
- Assignees: Samsung Display Co., Ltd.; Industry-Academic Cooperation Foundation Gyeongsang National University
- Inventors: Mi-Kyung Kim; Chang-Woong Chu; Jae-Young Hwang; Yun-Hi Kim; Soon-Ki Kwon
- Web page: https://patentgrep.com/patent/US20140191207A1

## CPC

- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- C09K 11/06: containing organic luminescent materials
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A silicon based compound and an organic light-emitting diode including the same.

## Claims

### Claim 1

A silicon-based compound represented by Formula 1:
L1 is a substituted or unsubstituted C6-C60 arylene group or a substituted or unsubstituted heteroarylene group;
a is an integer of 1 to 5 when a is 2 or more, a plurality of L1 may be identical to or different from each other;
R1 and R2 are, each independently, a C1-C60 alkyl group substituted with at least one —F;
b and c are, each independently, an integer of 0 to 4, and b+c≧1;
R3 and R4 are, each independently, selected from,
a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C2-C60 heteroaryl group; and
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C2-C60 heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric add or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, and an isoquinolyl group;
R10 is selected from,
a C1-C60 alkyl group, a C2-C60 alkenyl group, and a C2-C60 alkynyl group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, and a C2-C60 alkynyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic add or a salt thereof, and a phosphoric add or a salt thereof;
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C2-C60 heteroaryl group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C2-C60 heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof, C1-C60 alkyl group, C2-C60 alkenyl group, C2-C60 alkynyl group, C1-C60 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, and an isoquinolyl group; and
—N(Q11)(Q12), wherein Q11 and Q12 are, each independently, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, or a C2-C60 heteroaryl group; and
n is selected from an integer of 2 to 4.

### Claim 2 (depends on 1)

The silicon-based compound of claim 1, wherein
L1 is selected from,
i) phenylene, pentalenylene, indenylene, naphtylene, azulenylene, heptalenylene, indacenylene, acenaphtylene, fluorenylene, spiro-fluorenylene, phenalenylene, phenanthrenylene, anthrylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzooxazolylene, benzoimidazolylene, furanylene, benzofuranylene, thiophenylene, benzothiophenylene, thiazolylene, isothiazolylene, benzothiazolylene, isoxazolylene, oxazolylene, triazolylene, tetrazolylene, oxadiazolylene, triazinylene, benzoxazolylene, dibenzofuranylene, dibenzothiophenylene, and benzocarbazolylene; and
ii) phenylene, pentalenylene, indenylene, naphtylene, azulenylene, heptalenylene, indacenylene, acenaphtylene, fluorenylene, spiro-fluorenylene, phenalenylene, phenanthrenylene, anthrylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzooxazolylene, benzoimidazolylene, furanylene, benzofuranylene, thiophenylene, benzothiophenylene, thiazolylene, isothiazolylene, benzothiazolylene, isoxazolylene, oxazolylene, triazolylene, tetrazolylene, oxadiazolylene, triazinylene, benzoxazolylene, dibenzofuranylene, dibenzothiophenylene, and benzocarbazolylene, each substituted with at least one of
a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;
a C6-C20 aryl group and a C2-C20 heteroaryl group; and
a C6-C20 aryl group and a C2-C20 heteroaryl group, each substituted with at least one of a deuterium n atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidine group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, triazinyl group, quinolyl, and isoquinolyl, and
a is 1 or 2.

### Claim 3 (depends on 1)

The silicon-based compound of claim 1, wherein
L1 is selected from Formulae 2-1 to 2-8 below:
Z1 to Z4 are, each independently, selected from
a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof; and
phenyl group, naphthyl, and anthryl;
d1 is an integer of 1 to 4;
d2 is an integer of 1 to 3;
d3 is an integer of 1 to 6;
d4 is an integer of 1 to 8;
* is a binding site with Si of Formula 1 or is a binding site with a neighboring L1; and
*′ is a binding site with “N” of carbazol of Formula 1 or a binding site of a neighboring L1.

### Claim 4 (depends on 1)

The silicon-based compound of claim 1, wherein R1 and R2 are each independently a C1-C60 perfluoro alkyl group.

### Claim 5 (depends on 1)

The silicon-based compound of claim 1, wherein R1 and R2 are each independently selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl, each substituted with at least one —F.

### Claim 6 (depends on 1)

The silicon-based compound of claim 1, wherein R1 and R2 are each independently selected from —CF3, —C2F5, —C3F7, —C4F9, —C5F11, and —C6F13.

### Claim 7 (depends on 1)

The silicon-based compound of claim 1, wherein b and c are each independently, 0, 1, or 2, and b+c≧1.

### Claim 8 (depends on 1)

The silicon-based compound of claim 1, wherein
R3 and R4 are, each independently, selected from,
a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C10 alkyl group, and a C1-C10 alkoxy group;
a C1-C10 alkyl group and a C1-C10 alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;
phenyl, naphthyl, anthryl, fluorenyl, phenanthrenyl, pyrenyl, and chrysenyl; and
phenyl, naphthyl, anthryl, fluorenyl, phenanthrenyl, pyrenyl, and chrysenyl, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, and an isoquinolyl group.

### Claim 9 (depends on 1)

The silicon-based compound of claim 1, wherein R3 and R4 are hydrogen atoms.

### Claim 10 (depends on 1)

The silicon-based compound of claim 1, wherein R10 is selected from is selected from,
a C1-C10 alkyl group;
a C1-C10 alkyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;
phenyl, naphthyl, anthryl, fluorenyl, phenanthrenyl, pyrenyl and chrysenyl; and
phenyl, naphthyl, anthryl, fluorenyl, phenanthrenyl, pyrenyl, and chrysenyl, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, and an isoquinolyl group.

### Claim 11 (depends on 1)

The silicon-based compound of claim 1, wherein n is 2.

### Claim 12 (depends on 1)

The silicon-based compound of claim 1, wherein the silicon-based compound is represented by one of Formulae 1A to 1F below:
in Formulae 1A to 1F,
R1 and R7 are, each independently, selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl, each substituted with at least one —F;
R10 is selected from,
a C1-C10 alkyl group;
a C1-C10 alkyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;
phenyl, naphthyl, anthryl, fluorenyl, phenanthrenyl, pyrenyl and chrysenyl; and
phenyl, naphthyl, anthryl, fluorenyl, phenanthrenyl, pyrenyl, and chrysenyl, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric add or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, and an isoquinolyl group; and
n is an integer of 2 to 4.

### Claim 13 (depends on 12)

The silicon-based compound of claim 12, wherein R1 and R2 are each independently selected from —CF3, —C2F5, —C3F7, —C4F9, —C5F11, and —C6F13, and n is 2.

### Claim 14 (depends on 1)

The silicon-based compound of claim 1, wherein a HOMO level absolute value of the silicon-based compound is 5.80 eV or more and a LUMO level absolute value of the silicon-based compound is 2.20 eV or more.

### Claim 15 (depends on 1)

The silicon-based compound of claim 1, wherein the silicon-based compound is one of Compounds 1 to 10 below:

### Claim 16 (depends on 1)

An organic light-emitting diode comprising: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and comprising an emission layer, wherein the organic layer comprises at least one of the silicon-based compound of claim 1.

### Claim 17 (depends on 16)

The organic light-emitting diode of claim 16, wherein the organic layer further comprises
i) at least one layer selected from a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function, a buffer layer, and an electron blocking layer between the first electrode and the emission layer, and
ii) at least one layer selected from a hole blocking layer, an electron transport layer, and an electron injection layer interposed between the emission layer and the second electrode.

### Claim 18 (depends on 17)

The organic light-emitting diode of claim 17, wherein the emission layer comprises the silicon-based compound.

### Claim 19 (depends on 18)

The organic light-emitting diode of claim 18, wherein the emission layer further comprises a blue phosphorescent dopant for emitting blue light based on a phosphorescent light emission mechanism, and wherein the silicon-based compound in the emission layer acts as a host.

### Claim 20 (depends on 17)

The silicon-based compound of claim 17, wherein at least one of the hole injection layer, the hole transport layer, and the functional layer having a hole injection function and a hole transport function comprises a charge-generation material.