IP Library › Granted Patent US 10,147,884

Granted Patent B2

US 10,147,884 · App. 15/147,785 · Granted Dec 4, 2018

Organic light-emitting device

Inventors: Mieun Jun (Yongin-si, KR); Haejin Kim (Yongin-si, KR); Youngkook Kim (Yongin-si, KR); Seokhwan Hwang (Yongin-si, KR)

Assignee: Samsung Display Co., Ltd.

H01L51/006 C09K11/025 C09K11/06 H01L51/0056 H01L51/0058 H01L51/0061 H01L51/0094 C09K2211/1007 C09K2211/1011 C09K2211/1014 C09K2211/1088 C09K2211/1096 H01L51/0055 H01L51/0071 H01L51/0073 H01L51/5012 H01L51/5206 H01L51/5221

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Quick Facts

Patent No.: US 10,147,884
App. No.: 15/147,785
Granted: Dec 4, 2018
Kind: B2

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Abstract

According to one or more embodiments, 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 organic layer may include a first compound represented by Formula 1 and a second compound represented by one selected from Formula 2-1 to 2-4:

Claims (179)

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 including an emission layer,

wherein the organic layer comprises a first compound represented by Formula 1 and a second compound represented by one selected from Formulae 2-1 to 2-4:

wherein, in Formulae 1, A, and 2-1 to 2-4,

R 1 , R 3 to R 8 and R 10 to R 12 are each independently selected from a group represented by Formula A, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 );

at least one selected from R 1 , R 3 to R 8 and R 10 to R 12 is the group represented by Formula A;

R 2 and R 9 are each independently hydrogen;

Ar 211 and Ar 212 are each independently selected from a naphthalene group, an anthracene group, a triphenylene group, a pyrene group, a chrysene group, and a perylene group;

Ar 241 is selected from a benzene group, a biphenyl group, and a triphenylene group;

L 101 , L 211 to L 213 , L 221 , L 231 to L 234 , and L 241 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

a101 is selected from 0, 1, 2, and 3;

a211 to a213, a221, a231 to a234, and a241 are each independently selected from 0, 1, and 2;

R 101 , R 102 , R 231 to R 234 , and R 241 are each independently selected from 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 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;

b231 to b234 and b241 are each independently selected from 1, 2, and 3;

R 211 , R 212 , R 221 , R 222 , R 235 to R 238 , and R 242 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 );

b211, b212, b221, b222, b235 to b238, and b242 are each independently selected from 1, 2, and 3;

n211, n212 and n221 are each independently selected from 1, 2, and 3;

n231 to n234 are each independently selected from 0, 1, and 2;

a sum of n231 to n234 is selected from 1, 2, 3, 4, 5, and 6; and

n241 is selected from 3, 4, 5, 6, 7, and 8,

wherein Q 1 to Q 3 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

2. The organic light-emitting device of claim 1 , wherein

the first compound and the second compound are each comprised in the emission layer.

3. The organic light-emitting device of claim 1 , wherein

R 1 , R 3 to R 8 and R 10 to R 12 are each independently selected from the group consisting of:

the group represented by Formula A, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, and a cyclohexyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;

—Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),

wherein Q 1 to Q 3 are each independently selected from a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

4. The organic light-emitting device of claim 1 , wherein

R 3 and R 10 are each independently the group represented by Formula A;

R 3 and R 8 are each independently the group represented by Formula A;

R 1 and R 10 are each independently the group represented by Formula A; or

R 1 and R 8 are each independently the group represented by Formula A.

5. The organic light-emitting device of claim 1 , wherein

Ar 211 and Ar 212 are each independently an anthracene group.

6. The organic light-emitting device of claim 1 , wherein

L 101 , L 211 to L 213 , L 221 , L 231 to L 234 , and L 241 are each independently selected from the group consisting of:

a phenylene group, a naphthylene group, a fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, an indolylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, a benzimidazolylene group, a benzofuranylene group, a benzothiophenylene group, a triazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group.

7. The organic light-emitting device of claim 1 , wherein

L 101 , L 211 to L 213 , L 221 , L 231 to L 234 , and L 241 are each independently selected from groups represented by Formulae 3-1 to 3-31:

wherein, in Formulae 3-1 to 3-31,

Y 31 is selected from C(R 33 )(R 34 ), N(R 33 ), O, and S;

R 31 to R 34 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;

a31 is selected from 1, 2, 3, and 4;

a32 is selected from 1, 2, 3, 4, 5, and 6;

a33 is selected from 1, 2, 3, 4, 5, 6, 7, and 8;

a34 is selected from 1, 2, 3, 4, and 5;

a35 is selected from 1, 2, and 3; and

each of * and *′ indicates a binding site to a neighboring atom.

8. The organic light-emitting device of claim 1 , wherein

a101, a211 to a213, a221, a231 to a234, and a241 are each independently selected from 0 and 1.

9. The organic light-emitting device of claim 1 , wherein

R 101 and R 102 are each independently selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, and —Si(Q 31 )(Q 32 )(Q 33 ); and

wherein Q 31 to Q 33 are each independently selected from a C 1 -C 20 alkyl group, a C 6 -C 60 aryl group, a biphenyl group, and a terphenyl group.

10. The organic light-emitting device of claim 1 , wherein

R 101 and R 102 are each independently selected from groups represented by Formulae 5-1 to 5-32:

wherein, in Formulae 5-1 to 5-32,

Y 51 iS selected from C(R 53 )(R 54 ), Si(R 53 )(R 54 ), N(R 53 ), O, and S; and

R 51 to R 54 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, —CD 3 , —CF 3 , a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, and —Si(Q 31 )(Q 32 )(Q 33 ),

wherein Q 31 to Q 33 are each independently selected from a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group;

a51 is selected from 1, 2, 3, 4, and 5;

a52 is selected from 1, 2, 3, 4, 5, 6, and 7;

a53 is selected from 1, 2, 3, 4, 5, and 6;

a54 is selected from 1, 2, and 3;

a55 is selected from 1, 2, 3, and 4; and

* indicates a binding site to a neighboring atom.

11. The organic light-emitting device of claim 1 , wherein

R 231 to R 234 and R 241 are each independently selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, and a naphthyl group.

12. The organic light-emitting device of claim 1 , wherein

R 231 to R 234 and R 241 are each independently selected from groups represented by Formulae 7-1 to 7-16:

wherein, in Formulae 7-1 to 7-16,

Y 71 is selected from C(R 73 )(R 74 ), N(R 73 ), O, and S;

R 71 to R 74 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, and a naphthyl group;

a71 is selected from 1, 2, 3, 4, and 5;

a72 is selected from 1, 2, 3, 4, 5, 6, and 7;

a73 is selected from 1, 2, 3, 4, 5, and 6;

a74 is selected from 1, 2, and 3;

a75 is selected from 1, 2, 3, and 4; and

* indicates a binding site to a neighboring atom.

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

R 211 , R 212 , R 222 ,R 235 to R 238 , and R 242 are each independently selected from the group consisting of:

hydrogen, deuterium, —F, —Cl, —Br, —I, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, and a C 1 -C 20 alkoxy group;

a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, and a C 1 -C 20 alkyl group, each substituted with at least one selected from the deuterium, —F, —Cl, —Br, —I, a phenoxy group, a phenylthio group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —N(Q 31 )(Q 32 ), —Si(Q 31 )(Q 32 )(Q 33 ), and —B(Q 31 )(Q 32 );

a phenoxy group, a phenythio group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group,a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronaenyl group, an ovalenyl 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 isoxzolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidnyl group, a pyridazinyl group, an isoindoly group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzfuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;

a phenoxy group, a phenylthio group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl 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 isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenoxy group, a phenylthio group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl 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 isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —N(Q 31 )(Q 32 ), —Si(Q 31 )(Q 32 )(Q 33 ), and —B(Q 31 )(Q 32 ); and

—Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), and —B(Q 1 )(Q 2 ),

wherein Q 1 to Q 3 and Q 31 to Q 33 are each independently selected from a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

14. The organic light-emitting device of claim 1 , wherein

R 211 , R 212 , R 221 , R 222 , R 235 to R 238 , and R 242 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, 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 methoxy group, an ethoxy group, an iso-propoxy group, an n-butoxy group, an iso-butoxy group, a sec-butoxy group, a tert-butoxy group, —Si(CH 3 ) 3 , —Si(Ph) 3 , —N(Ph 2 ) 2 , —B(Ph) 2 , and a group represented by any of Formulae 9-1 to 9-15:

wherein, in Formulae 9-1 to 9-15,

Y 91 is selected from C(R 96 )(R 97 ), N(R 96 ), O, and S;

R 91 to R 93 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a phenoxy group, a phenylthio group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group;

R 94 to R 97 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenoxy group, a phenylthio group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a91 is selected from 1, 2, 3, 4, and 5;

a92 is selected from 1, 2, 3, 4, 5, 6, and 7;

a93 is selected from 1, 2, 3, 4, 5, and 6;

a94 is selected from 1, 2, and 3;

a95 is selected from 1, 2, 3, and 4; and

* indicates a binding site to a neighboring atom.

15. The organic light-emitting device of claim 1 , wherein

the first compound is represented by Formula 1-1:

wherein, in Formula 1-1,

R 1 , R 3 , R 8 , and R 10 are each independently selected from the group represented by Formula A, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ); and

at least one selected from R 1 , R 3 , R 8 , and R 10 is the group represented by Formula A,

16. The organic light-emitting device of claim 1 , wherein

the first compound represented by Formula 1 is selected from Compounds 1 to 153:

17. The organic light-emitting device of claim 1 , wherein

the second compound is represented by one selected from Formulae 2-11 to 2-16:

wherein, in Formulae 2-11 to 2-16,

Ar 241 , L 211 to L 213 , L 221 , L 231 to L 234 , L 241 , a211 to a213, a221, a231 to a234, a241, R 231 to R 234 , R 241 , b231 to b234, b241, R 211 , R 212 , R 221 , R 222 , R 235 to R 238 , R 242 , b211, b212, b221, b222, b235 to b238, b242, n211, and n212 are each independently the same as respectively described in connection with Formulae 2-1 to 2-4;

R 243 to R 247 are each independently the same as described in connection with R 241 in Formula 2-3;

b243 to b247 are each independently the same as described in connection with b241 in Formula 2-4;

L 222 is the same as described in connection with L 221 in Formula 2-2;

a222 is the same as described in connection with a221 in Formula 2-2;

R 223 is the same as described in connection with R 221 in Formula 2-2;

b223 is the same as described in connection with b221 in Formula 2-2;

L 242 to L 246 are each independently the same as described in connection with L 241 in Formula 2-4; and

a242 to a246 are each independently the same as described in connection with a241 in Formula 2-4.

18. The organic light-emitting device of claim 1 , wherein

the second compound is represented by one selected from Formulae 2-21 to 2-29:

wherein, in Formulae 2-21 to 2-29,

L 211 to L 213 , L 221 , L 231 to L 234 , L 241 , a211 to a213, a221, a231 to a234, a241, R 231 to R 234 , R 241 , b231 to b234, b241, R 211 , R 212 , R 221 , R 222 , R 235 to R 238 , R 242 , b211, b212, b221, b222, b235 to b238, b242, n211, and n212 are each independently the same as respectively described in connection with Formulae 2-1 to 2-4;

R 224 is the same as described in connection with R 222 in Formula 2-2;

L 222 is the same as described in connection with L 221 in Formula 2-2;

a222 is the same as described in connection with a221 in Formula 2-2;

R 223 is the same as described in connection with R 221 in Formula 2-2;

b223 is the same as described in connection with b221 in Formula 2-2;

L 242 to L 246 are each independently the same as described in connection with L 241 in Formula 2-4;

a242 to a246are each independently the same as described in connection with a241 in Formula 2-4;

R 243 to R 247 are each independently the same as described in connection with R 241 in Formula 2-4;

R 248 and R 249 are each independently the same as described in connection with R 242 in Formula 2-4;

b243 to b247 are each independently the same as described in connection with b241 in Formula 2-4; and

b248 and b249 are each independently the same as described in connection with b242 in Formula 2-4.

19. 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 including an emission layer,

wherein the organic layer comprises a first compound represented by Formula 1 and a second compound selected from Compounds H-1 to H-68:

wherein, in Formulae 1 and A,

R 1 to R 12 are each independently selected from a group represented by Formula A, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 );

at least one selected from R 1 to R 12 is the group represented by Formula A;

L 101 is selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

a101 is selected from 0, 1, 2, and 3;

R 101 and R 102 are each independently selected from 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 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;

wherein Q 1 to Q 3 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group:

20. The organic light-emitting device of claim 2 , wherein

the first compound is a dopant, and the second compound is a host.

21. 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 including an emission layer,

wherein the organic layer comprises a first compound represented by Formula 1 and a second compound represented by one selected from Formulae 2-3 to 2-4:

wherein in Formulae 1, A, 2-3 and 2-4,

R 1 to R 12 are each independently selected from a group represented by Formula A, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 );

at least one selected from R 1 to R 12 is the group represented by Formula A;

Ar 241 is selected from a benzene group, a biphenyl group, and a triphenylene group;

L 101 , L 231 to L 234 , and L 241 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

a101 is selected from 0, 1, 2, and 3;

a231 to a234, and a241 are each independently selected from 0, 1, and 2;

b231 to b234 and b241 are each independently selected from 1, 2, and 3;

R 235 to R 238 , and R 242 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O) (Q 1 )(Q 2 );

b235 to b238, and b242 are each independently selected from 1, 2, and 3;

n211, n212 and n221 are each independently selected from 1, 2, and 3;

n231 to n234 are each independently selected from 0, 1, and 2;

a sum of n231 to n234 is selected from 1, 2, 3, 4, 5, and 6; and

n241 is selected from 3, 4, 5, 6, 7, and 8,

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 9, 2016

From: JUN, MIEUN; KIM, HAEJIN; KIM, YOUNGKOOK; HWANG, SEOKHWAN

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 038521/0538 →

Continuity (1)

Related Publication 20160329494A1 · Nov 10, 2016