IP Library › Granted Patent US 10,158,085

Granted Patent B2

US 10,158,085 · App. 14/573,422 · Granted Dec 18, 2018

Condensed cyclic compound and organic light-emitting device including the same

Inventors: Seungjae Lee (Suwon-si, KR); Byungku Kim (Suwon-si, KR); Youngkwon Kim (Suwon-si, KR); Changwoo Kim (Suwon-si, KR); Hyungsun Kim (Suwon-si, KR); Changju Shin (Suwon-si, KR); Eunsun Yu (Suwon-si, KR); Byoungki Choi (Hwaseong-si, KR); Kyuyoung Hwang (Ansan-si, KR)

Assignees: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.

H01L51/0067 H01L51/0072 H01L51/0073 H01L51/0081 H01L51/0085 H01L51/5016

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Quick Facts

Patent No.: US 10,158,085
App. No.: 14/573,422
Granted: Dec 18, 2018
Kind: B2

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Abstract

A condensed-cyclic compound represented by Formula 1A or 1B: wherein in Formulae 1A and 1B, groups, substituents, and variables are the same as defined in the specification.

Claims (101)

1. A condensed-cyclic compound represented by Formula 1B:

wherein in Formula 1B,

ring A 1 is represented by Formula 1C;

X 1 is N or C-[(L 1 ) a1 -(R 1 ) b1 ],

X 2 is N or C-[(L 2 ) a2 -(R 2 ) b2 ],

X 3 is N or C-[(L 3 ) a3 -(R 3 ) b3 ], and

at least one of X 1 to X 3 is N;

X 4 is O or S;

X 11 is selected from N-[(L 12 ) a12 -(R 12 ) b12 ], S, O, S(═O), S(═O) 2 , C(═O), C(R 13 )(R 14 ), Si(R 13 )(R 14 ), P(R 13 ), P(═O)(R 13 ), and C═N(R 12 );

L 1 to L 4 , L 11 , L 12 , and L 21 are each independently selected from Formulae 2-1 to 2-34;

a1 to a4, a11, a12, and a21 are each independently selected from integers of 0 to 3;

R 1 to R 3 , R 5 , R 6 , and R 13 to R 17 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;

a C 1 -C 20 alkyl group and a C 1 -C 20 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 or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;

a phenyl 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 isooxazolyl 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 benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, —Si(Q 33 )(Q 34 )(Q 35 ), a phenyl 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 isooxazolyl 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 benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and a biphenyl group,

R 4 , R 11 , and R 12 are each independently selected from:

a phenyl 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 hexacencyl 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 isooxazolyl group, a pyridinyl group, a pyranzinyl 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 benzoquinolinyl group a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, —Si(Q 33 )(Q 34 )(Q 35 ), a phenyl 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 isooxazolyl 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 benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and a biphenyl group,

b1 to b6 and b11 to b17 are each independently selected from integers of 1 to 3;

wherein in Formulae 2-1 to 2-34,

Y 1 is O, S, S(═O), S(═O) 2 , C(Z 3 )(Z 4 ), N(Z 5 ) or Si(Z 6 )(Z 7 );

Z 1 to Z 7 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and —Si(Q 33 )(Q 34 )(Q 35 ),

wherein Q 33 to Q 35 are each independently selected from a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group; and

d1 is selected from integers of 1 to 4,

d2 is selected from integers of 1 to 3,

d3 is selected from integers of 1 to 6,

d4 is selected from integers of 1 to 8,

d5 is 1 or 2,

d6 is selected from integers of 1 to 5, and

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

2. The condensed-cyclic compound of claim 1 , wherein the condensed-cyclic compound is represented by one of Formulae and 1 B-1 to 1 B-4:

wherein in Formulae 1B-1 to 1B-4, X 1 to X 4 , X 11 , L 1 to L 4 , L 11 , L 12 , L 21 , a1 to a4, a11, a12, a21, R 1 to R 6 , R 11 to R 17 , b1 to b6, and b11 to b17 are the same as described in claim 1 .

3. The condensed-cyclic compound of claim 1 , wherein the condensed-cyclic compound is represented by one of Formulae 1B(1), 1B(2), and 1B(4):

wherein in Formulae 1B(1), 1B(2), and 1B(4), the ring A 1 is represented by Formula 1C and descriptions of X 1 to X 4 , X 11 , L 1 to L 4 , L 11 , L 12 , L 21 , a1 to a4, a11, a12, a21, R 1 to R 6 , R 11 to R 17 , b1 to b6, and b11 to b17 are the same as described in claim 1 .

4. The condensed-cyclic compound of claim 1 , wherein

X 1 to X 3 is N;

X 1 is C-[(L 1 ) a1 -(R 1 ) b1 ] and X 2 and X 3 are N;

X 1 is N, X 2 is C-[(L 2 ) a2 -(R 2 ) b2 ], and X 3 is N;

X 1 and X 2 are N and X 3 is C-[(L 3 ) a3 -(R 3 ) b3 ];

X 1 is C-[(L 1 ) a1 -(R 1 ) b1 ], X 2 is N, and X 3 is C-[(L 3 ) a3 -(R 3 ) b3 ];

X 1 is C-[(L 1 ) a1 -(R 1 ) b1 ], X 2 is C-[(L 2 ) a2 -(R 2 ) b2 ], and X 3 is N; or

X 1 is N, X 2 is C-[(L 2 ) a2 -(R 2 ) b2 ], and X 3 is C-[(L 3 ) a3 -(R 3 ) b3 ].

5. The condensed-cyclic compound of claim 1 , wherein

X 1 is C-[(L 1 ) a1 -(R 1 ) b1 ] and X 2 and X 3 are N; or

X 1 and X 2 are N, and X 3 is C-[(L 3 ) a3 -(R 3 ) b3 ].

6. The condensed-cyclic compound of claim 1 , wherein a21 is 1.

7. The condensed-cyclic compound of claim 1 , wherein

R 1 to R 3 , R 5 , R 6 , and R 13 to R 17 are each independently selected from:

Formulae 4-1 to 4-31; and

—Si(Q 3 )(Q 4 )(Q 5 ), provided that R 13 and R 14 are not —Si(Q 3 )(Q 4 )(Q 5 ),

R 4 , R 11 , and R 12 are each independently selected from Formulae 4-1 to 4-31:

in Formula 4-1 to 4-31,

Y 31 is O, S, C(Z 33 )(Z 34 ), N(Z 35 ) or Si(Z 36 )(Z 37 );

Z 31 to Z 37 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and —Si(Q 33 )(Q 34 )(Q 35 );

Q 3 to Q 5 and Q 33 to Q 35 are each independently selected from a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group;

e1 is selected from integers of 1 to 5,

e2 is selected from integers of 1 to 7,

e3 is selected from integers of 1 to 3,

e4 is selected from integers of 1 to 4,

e5 is 1 or 2, and

e6 is selected from integers of 1 to 6, and

* indicates a bonding site to a neighboring atom.

8. The condensed-cyclic compound of claim 1 , wherein

R 1 to R 3 , R 5 , R 6 , and R 13 to R 17 are each independently selected from:

a phenyl group and a naphthyl group; and

a phenyl group and a naphthyl 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, and a naphthyl group; and

R 4 , R 11 , and R 12 are each independently selected from:

a phenyl group and a naphthyl group; and

9. An organic light-emitting device comprising

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer comprises an emission layer and the condensed-cyclic compound of claim 1 .

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

the first electrode is an anode and

the second electrode is a cathode,

wherein the organic layer comprises

i) a hole transport region disposed between the first electrode and the emission layer,

wherein the hole transport region comprises at least one of a hole-injection layer, a hole-transporting layer, and an electron-blocking layer; and

ii) an electron transport region disposed between the emission layer and the second electrode,

wherein the electron transport region comprises at least one layer selected from a hole-blocking layer, an electron-transporting layer, and an electron-injecting layer.

11. The organic light-emitting device of claim 9 , wherein the emission layer comprises the condensed-cyclic compound.

12. The organic light-emitting device of claim 11 , wherein the emission layer further comprises an organometallic compound represented by Formula 81:

wherein in Formula 81,

M is selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm;

Y 1 to Y 4 are each independently C or N;

Y 1 and Y 2 are connected by a single bond or a double bond and

Y 3 and Y 4 are connected by a single bond or a double bond;

CY 1 and CY 2 are each independently selected from a benzene, a naphthalene, a fluorene, a spiro-fluorene, an indene, a pyrrole, a thiophene, a furan, an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isooxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, a quinoline, an isoquinoline, a benzoquinoline, a quinoxaline, a quinazoline, a carbazole, a benzoimidazole, a benzofuran, a benzothiophene, an isobenzothiophene, a benzooxazole, an isobenzooxazole, a triazole, a tetrazole, an oxadiazole, a triazine, a dibenzofuran, and a dibenzothiophene, wherein CY 1 and CY 2 are optionally bound to each other by a single bond or an organic linking group;

R 81 and R 82 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, —SF 5 , 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 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -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 2 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group, —N(Q 1 )(O 2 ), —Si(Q 3 )(O 4 )(Q 5 ), and —B(Q 6 )(Q 7 );

a81 and a82 are each independently selected from integers of 1 to 5;

n81 is selected from integers of 0 to 4;

n82 is 1, 2, or 3; and

L81 is selected from a monovalent organic ligand, a divalent organic ligand, and a trivalent organic ligand.

13. A condensed-cyclic compound being one of the following compounds:

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2015

From: LEE, SEUNGJAE; KIM, BYUNGKU; KIM, YOUNGKWON; KIM, CHANGWOO; KIM, HYUNGSUN; SHIN, CHANGJU; YU, EUNSUN; CHOI, BYOUNGKI; HWANG, KYUYOUNG

To: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.

Reel/Frame 035317/0721 →

Priority Claims (1)

KR 10-2013-0157532 · Dec 17, 2013 · national

Continuity (1)

Related Publication 20150171340A1 · Jun 18, 2015

Cited By (1)

US 12,583,843