# US 2014/0191214 A1 · Fluorene-based compound and organic light-emitting device including the same

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- Number: US 2014/0191214 A1
- Document ID: US20140191214A1
- Status: Published application
- Kind: A1
- Application number: 14/134,450
- Filed: 2013-12-19
- Published: 2014-07-10
- Earliest claimed: 2013-01-04
- Assignees: Samsung Display Co., Ltd.
- Applicants: Samsung Display Co., Ltd.
- Inventors: Hee-Yeon Kim
- Web page: https://patentgrep.com/patent/US20140191214A1

## CPC

- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 50/15: Hole transporting layers
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A fluorene-based compound represented by Formula 1 below and an organic light-emitting device (OLED) including the fluorene-based compound. wherein R1 to R3, R10 to R17 and a, b, c, d, e, and f are defined as in the specification.

## Claims

### Claim 1

A fluorene-based compound represented by Formula 1 below:
wherein R1 to R3 are each independently selected from a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group, and R2 and R3 are optionally connected to each other by a single bond, —O, —S—, a substituted or unsubstituted C1-C5 alkylene group, or a substituted or unsubstituted C2-C5 alkenylene group;
R10 to R17 are each independently selected from hydrogen, deuterium, 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 group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C3-C10 heterocycloalkyl group, a substituted or unsubstituted C2-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthiogroup, a substituted or unsubstituted C2-C60 heteroaryl group, —N(Q))(Q2), and —Si(Q3)(Q4)(Q5), and Q1 to Q5 are each independently selected from hydrogen, deuterium, 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 group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C3-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthiogroup, and a substituted or unsubstituted C2-C60 heteroaryl group;
a, c, and d are each independently an integer between 1 to 3; and
b, e, and f are each independently an integer between 1 to 4.

### Claim 2 (depends on 1)

The fluorene-based compound according to claim 1, wherein R1 to R3 are each independently selected from a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, an isothiazolyl group, an isoxazole group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a phenyl group, a pyrydinyl group, a pyrazinyl group, a pyrymidinyl group, a pyrydazinyl group, a triazinyl group, a pentalenyl group, an indenyl group, a naphtyl group, an azulenyl group, a heptalenyl group, a biphenyl group, an indacenyl group, an acenaphthylenyl group, a fluorenyl group, a spirofluorenyl group, a carbazolyl group, an anthryl group, a phenalenyl group, a phenanthrenyl group, a pherylenyl group, a fluoranthenyl group, a naphtalsenyl group, a picenyl group, a pentaphenyl group, a hexacenyl group, a dibenzofuranyl group, a dibenzotiophenyl group, a phenothiazinyl group, a phenoxazinyl group, a dihydrophenazinyl group, a phenoxathinyl group, and a phenanthridinyl group; and
a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, an isothiazolyl group, an isoxazole group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a phenyl group, a pyrydinyl group, a pyrazinyl group, a pyrymidinyl group, a pyrydazinyl group, a triazinyl group, a pentalenyl group, an indenyl group, a naphtyl group, an azulenyl group, a heptalenyl group, a biphenyl group, an indacenyl group, an acenaphthylenyl group, a fluorenyl group, a spirofluorenyl group, a carbazolyl group, an anthryl group, a phenalenyl group, a phenanthrenyl group, a pherylenyl group, a fluoranthenyl group, a naphtalsenyl group, a picenyl group, a pentaphenyl group, a hexacenyl group, a dibenzofuranyl group, a dibenzotiophenyl group, a phenothiazinyl group, a phenoxazinyl group, a dihydrophenazinyl group, a phenoxathinyl group, and a phenanthridinyl group, substituted with at least one of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group 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 C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthiogroup, a C2-C60 heteroaryl group, a phenyl-C2-C60 heteroaryl group, and —N(Q11)(Q12) (herein, Q11 and Q12 are each independently hydrogen, a C1-C10 alkyl group, a C6-C20 aryl group, or a C2-C20 heteroaryl group).

### Claim 3 (depends on 1)

The fluorene-based compound according to claim 1, wherein R1 to R3 are each independently selected from a phenyl group, a pyrydinyl group, a pyrazinyl group, a pyrymidinyl group, a pyrydazinyl group, a triazinyl group, a naphtyl group, a fluorenyl group, a spirofluorenyl group, a carbazolyl group, an anthryl group, a phenalenyl group, and a phenanthrenyl group; and
a phenyl group, a pyrydinyl group, a pyrazinyl group, a pyrymidinyl group, a pyrydazinyl group, a triazinyl group, a naphtyl group, a fluorenyl group, a spirofluorenyl group, a carrbazolyl group, an anthryl group, a phenalenyl group, and a phenanthrenyl group, substituted with at least one of deuterium, 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 group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphtyl group, an anthryl group, a phenyl-carbazolyl group, a pyrydinyl group, a pyrymidinyl group, and a pyrazinyl group.

### Claim 4 (depends on 1)

The fluorene-based compound according to claim 1, wherein R1 to R3 are each independently selected from a phenyl group; a dimethylfluorenyl group; a biphenyl group; a naphtyl group; a phenyl-carbazolyl group; a phenyl group substituted with a phenyl-carbazolyl group, and an anthryl group.

### Claim 5 (depends on 1)

The fluorene-based compound according to claim 1, wherein R2 and R3 are connected to each other by a single bond.

### Claim 6 (depends on 1)

The fluorene-based compound according to claim 1, wherein R10 and R11 are each independently selected from a C1-C60 alkyl group and a C6-C14 aryl group; and
a C1-C60 alkyl group and a C6-C14 aryl group, substituted with at least one of deuterium, 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 group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphtyl group, and an anthryl group.

### Claim 7 (depends on 1)

The fluorene-based compound according to claim 1, wherein R10 and R11 are each independently selected from a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonenyl group, an isononenyl group, a sec-nonenyl group, a tert-nonenyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group;
a phenyl group, a naphtyl group, and an anthryl group; and
a phenyl group, a naphtyl group, and an anthryl group, substituted with at least one of deuterium, 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 group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonenyl group, an isononenyl group, a sec-nonenyl group, a tert-nonenyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a phenyl group, a naphtyl group, and an anthryl group.

### Claim 8 (depends on 1)

The fluorene-based compound according to claim 1, wherein R10 and R11 are connected to each other by a single bond.

### Claim 9 (depends on 1)

The fluorene-based compound according to claim 1, wherein R12 to R17 are each independently selected from hydrogen, deuterium, 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 group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonenyl group, an isononenyl group, a sec-nonenyl group, a tert-nonenyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a phenyl group, a naphtyl group, and an anthryl group.

### Claim 10 (depends on 1)

The fluorene-based compound according to claim 1, wherein R12 to R17 are hydrogen atoms.

### Claim 11 (depends on 1)

The fluorene-based compound according to claim 1, wherein the fluorene-based compound is represented by Formula 1A:
wherein R1 to R3 are each independently selected from a phenyl group, a pyrydinyl group, a pyrazinyl group, a pyrymidinyl group, a pyrydazinyl group, a triazinyl group, a naphtyl group, a fluorenyl group, a spirofluorenyl group, a carbazolyl group, an anthryl group, a phenalenyl group, and a phenanthrenyl group; and
a phenyl group, a pyrydinyl group, a pyrazinyl group, a pyrymidinyl group, a pyrydazinyl group, a triazinyl group, a naphtyl group, a fluorenyl group, a spirofluorenyl group, a carbazolyl group, an anthryl group, a phenalenyl group, and a phenanthrenyl group, substituted with at least one of deuterium, 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 group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphtyl group, an anthryl group, a phenyl-carbazolyl group, a pyrydinyl group, a pyrymidinyl group, and a pyrazinyl group;
R10 and R11 are each selected from a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonenyl group, an isononenyl group, a sec-nonenyl group, a tert-nonenyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group;
a phenyl group, a naphtyl group, and an anthryl group; and
a phenyl group, a naphtyl group, and an anthryl group, substituted with at least one of deuterium, 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 group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonenyl group, an isononenyl group, a sec-nonenyl group, a tert-nonenyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a phenyl group, a naphtyl group, and an anthryl group.

### Claim 12 (depends on 1)

The fluorene-based compound according to claim 1, wherein the fluorene-based compound is represented by Formula 1B:
wherein R1 is selected from a phenyl group, a pyrydinyl group, a pyrazinyl group, a pyrymidinyl group, a pyrydazinyl group, a triazinyl group, a naphtyl group, a fluorenyl group, a spirofluorenyl group, a carbazolyl group, an anthryl group, a phenalenyl group, and a phenanthrenyl group; and
a phenyl group, a pyrydinyl group, a pyrazinyl group, a pyrymidinyl group, a pyrydazinyl group, a triazinyl group, a naphtyl group, a fluorenyl group, a spirofluorenyl group, a carbazolyl group, an anthryl group, a phenalenyl group, and a phenanthrenyl group, substituted with at least one of deuterium, 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 group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphtyl group, an anthryl group a phenyl-carbazolyl group, a pyrydinyl group, a pyrymidinyl group, and a pyrazinyl group;
Z1 and Z2 are each independently selected from hydrogen, deuterium, 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 group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphtyl group, and an anthryl group;
p and q are each independently an integer between 1 to 4;
R10 and R11 are each independently selected from a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonenyl group, an isononenyl group, a sec-nonenyl group, a tert-nonenyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group;
a phenyl group, a naphtyl group, and an anthryl group; and
a phenyl group, a naphtyl group, and an anthryl group, substituted with at least one of deuterium, 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 group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonenyl group, an isononenyl group, a sec-nonenyl group, a tert-nonenyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a phenyl group, a naphtyl group, and an anthryl group.

### Claim 13 (depends on 1)

The fluorene-based compound according to claim 1, being one of Compounds 1 to 23:

### Claim 14 (depends on 1)

An organic light-emitting device comprising
a first electrode;
a second electrode disposed opposite to the first electrode; and
an organic layer disposed between the first electrode and the second electrode, and the organic layer comprising an emission layer (EML);
wherein the organic layer comprises at least one of the fluorene-based compounds of claim 1.

### Claim 15 (depends on 14)

The organic light-emitting device of claim 14, wherein the organic layer further comprises
at least one layer selected from among a hole injection layer (HIL), a hole transport layer (HTL), a functional layer having both hole injection and hole transport capabilities at the same time, a buffer layer, and an electron blocking layer (EBL) disposed between the first electrode and the EML, and
at least one layer selected from among a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL) disposed between the EML and the second electrode,
wherein the at least one layer disposed between the first electrode and the EML comprises the fluorene-based compound.

### Claim 16 (depends on 14)

The organic light-emitting device of claim 14, wherein the organic layer comprises an HTL disposed between the first electrode and the EML, and where the fluorene-based compound exists in the HTL.

### Claim 17 (depends on 15)

The organic light-emitting device of claim 15, wherein the at least one layer disposed between the first electrode and the EML further comprises a charge-generating material.

### Claim 18 (depends on 14)

The organic light-emitting device of claim 14, wherein the EML comprises an organometallic complex having at least one of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm.