IP Library Granted Patent US 10,128,443
Granted Patent B2
US 10,128,443 · App. 14/752,508 · Granted Nov 13, 2018

Organic light-emitting device

Inventors: Naoyuki Ito (Yongin, KR); Seulong Kim (Yongin, KR); Younsun Kim (Yongin, KR); Dongwoo Shin (Yongin, KR); Jungsub Lee (Yongin, KR)
Assignee: Samsung Display Co., Ltd.
H01L51/0058C09K11/025C09K11/06H01L27/3244H01L51/006H01L51/0061H01L51/0073C09K2211/1007C09K2211/1011C09K2211/1014H01L51/0054H01L51/0072H01L51/0074H01L2251/5384
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Quick Facts
Patent No.
US 10,128,443
App. No.
14/752,508
Granted
Nov 13, 2018
Kind
B2
Abstract

An organic light-emitting device includes a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer. The emission layer includes a first material represented by Formula 1 and a second material represented by Formula 2:

Claims (72)

1. An organic light-emitting device 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 emission layer comprises a first material represented by Formula 1 and a second material represented by Formula 2:

wherein in Formulae 1, 2, and 2A to 2C,

L 11 and L 12 are each independently selected from a substituted or unsubstituted C 6 -C 60 arylene group and a substituted or unsubstituted C 1 -C 60 heteroarylene group;

a11 and a12are each independently selected from 0, 1, 2, and 3;

R 11 and R 12 are each independently selected from: a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

b11 and b12 are each independently selected from 1, 2, and 3;

R 13 to R 20 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q 1 )(Q 2 )(Q 3 );

Ar 21 is selected from a mono, di or tri-valent substituted or unsubstituted C 6 -C 60 arene and a mono, di or tri-valent substituted or unsubstituted non-aromatic condensed polycycle, a valency of the C 6 -C 60 arene and the non-aromatic condensed polycycle corresponding to a value of n21;

R 21 and R 22 are each independently selected from R x , a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group, wherein at least one of R 21 and R 22 is R x and R x is a group represented by one of Formulae 2A to 2C above;

L 21 to L 24 are each independently selected from a substituted or unsubstituted C 6 -C 60 arylene group and a substituted or unsubstituted C 1 -C 60 heteroarylene group;

a21 to a24 are each independently selected from 0, 1, 2, and 3;

X 21 is selected from an oxygen atom (O), a sulfur atom (S), N(R 25 ), and C(R 25 )(R 26 );

R 23 to R 26 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

b23 and b24 are each independently selected from 1, 2, 3, and 4;

n21 is selected from 1, 2, and 3; and

at least one substituent of the substituted C 6 -C 60 arene, the substituted non-aromatic condensed polycycle, the substituted C 6 -C 60 arylene group, the substituted C 1 -C 60 heteroarylene group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:

a deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amino group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C 1 -C 60 alkyl group; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group and a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 );

a C 3 -C 10 cycloalkyl group; a C 1 -C 10 heterocycloalkyl group; a C 3 -C 10 cycloalkenyl group; a C 1 -C 10 heterocycloalkenyl group; a C 6 -C 60 aryl group; a C 6 -C 60 aryloxy group; a C 6 -C 60 arylthio group; a C 1 -C 60 heteroaryl group; a monovalent non-aromatic condensed polycyclic group; and a monovalent non-aromatic condensed heteropolycyclic group;

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ); and

—Si(Q 31 )(Q 32 )(Q 33 ); —N(Q 34 )(Q 35 ); and —B(Q 36 )(Q 37 ),

wherein Q 1 to Q 3 , Q 11 to Q 17 , Q 21 to Q 27 , and Q 31 to Q 37 are each independently selected from a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

2. The organic light-emitting device of claim 1 , wherein L 11 , L 12 and L 21 to L 24 are each independently selected from:

a phenylene group and a naphthylene group; and

a phenylene group and a naphthylene group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, a C 1 -C 20 alkyl group, a phenyl group, and a naphthyl group.

3. The organic light-emitting device of claim 1 , wherein L 11 , L 12 and L 21 to L 24 are each independently selected from groups represented by Formulae 3-1 to 3-15 below:

wherein in Formulae 3-1 to 3-15,

R 31 is selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a phenyl group, and a naphthyl group;

b31 is selected from 1, 2, 3, and 4;

b32 is selected from 1, 2, 3, 4, 5, and 6; and

* and *′ each indicate a binding site to a neighboring atom.

4. The organic light-emitting device of claim 1 , wherein R 11 and R 12 are each independently selected from a phenyl group; a naphthyl group; a fluorenyl group; a phenanthrenyl group; an anthracenyl group; a dibenzofuranyl group; and a dibenzothiophenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, phenanthrenyl group, an anthracenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one of a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a phenyl group, and a naphthyl group.

5. The organic light-emitting device of claim 1 , wherein R 11 and R 12 are each independently selected from groups represented by Formulae 5-1 to 5-26 below:

wherein in Formulae 5-1 to 5-26,

Ph is a phenyl group; and

* indicates a binding site to a neighboring atom.

6. The organic light-emitting device of claim 1 , wherein R 13 to R 20 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, and —Si(Q 1 )(Q 2 )(Q 3 ),

wherein Q 1 to Q 3 are each independently selected from a C 1 -C 60 alkyl group and a C 6 -C 60 aryl group.

7. The organic light-emitting device of claim 1 , wherein R 13 to R 20 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a phenyl group and —Si(CH 3 ) 3 .

8. The organic light-emitting device of claim 1 , wherein Ar 21 is selected from a mono, di or tri-valent benzene; a mono, di or tri-valent naphthalene; a mono, di or tri-valent anthracene; a mono, di or tri-valent phenanthrene; a mono, di or tri-valent a triphenylene; and a mono, di or tri-valent fluorene; and

a mono, di or tri-valent benzene, a mono, di or tri-valent naphthalene, a mono, di or tri-valent anthracene, a mono, di or tri-valent phenanthrene, a mono, di or tri-valent triphenylene, and a mono, di or tri-valent fluorene, each substituted with at least one of a methyl group, a phenyl group, and a naphthyl group.

9. The organic light-emitting device of claim 1 , wherein R 21 and R 22 are each independently selected from R x ; a phenyl group; a naphthyl group; a phenalenyl group; a phenanthrenyl group; an anthracenyl group; a triphenylenyl group; a pyrenyl group; a chrysenyl group; a perylenyl group; a hexacenyl group; a pentacenyl group; a thiophenyl group; a furanyl group; a benzofuranyl group; and a benzothiophenyl group; and

a phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a benzofuranyl group, and a benzothiophenyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, and —N(Q 34 )(Q 35 ),

wherein Q 34 and Q 35 are each independently a C 6 -C 60 aryl group, and at least one of R 21 and R 22 is R x.

10. The organic light-emitting device of claim 1 , wherein R 21 and R 22 are each independently selected from R x and a group represented by one of Formulae 6-1 to

6-10 below, and

at least one of R 21 and R 22 is R x :

wherein in Formulae 6-1 to 6-10,

Ph is a phenyl group; and

* indicates a binding site to a neighboring atom.

11. The organic light-emitting device of claim 1 , wherein R x , is represented by Formula 2A-1 below:

12. The organic light-emitting device of claim 1 , wherein R x , is selected from Formulae 7-1 to 7-24 below:

wherein in Formulae 7-1 to 7-24,

Ph is a phenyl group; and

* indicates a binding site to a neighboring atom.

13. The organic light-emitting device of claim 1 , wherein n21 is 1.

14. The organic light-emitting device of claim 1 , wherein the first material is represented by Formula 1-1 below:

15. The organic light-emitting device of claim 1 , wherein the second material is represented by Formula 2-1 below:

16. The organic light-emitting device of claim 1 , wherein the second material is represented by one of Formulae 2-11 and 2-12 below:

17. The organic light-emitting device of claim 1 , wherein the emission layer further comprises a fluorescent dopant.

18. The organic light-emitting device of claim 17 , wherein a maximum emission wavelength of the fluorescent dopant is in a range of about 400 nm to about 550 nm.

19. The organic light-emitting device of claim 1 , wherein the organic light-emitting device comprises one or more subpixels; and

each subpixel comprises a single emission layer.

20. The organic light-emitting device of claim 19 , further comprising:

a hole transport region and an electron transport region,

wherein the first electrode, the hole transport region, the emission layer, the electron transport region, and the second electrode are sequentially stacked.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 15, 2015
From: ITO, NAOYUKI; KIM, SEULONG; KIM, YOUNSUN; SHIN, DONGWOO; LEE, JUNGSUB
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 036101/0914 →
Priority Claims (1)
KR 10-2015-0010029 · Jan 21, 2015 · national
Continuity (1)
Related Publication 20160211458A1 · Jul 21, 2016