IP Library › Granted Patent US 10,593,891

Granted Patent B2

US 10,593,891 · App. 15/234,089 · Granted Mar 17, 2020

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

Inventors: Yeonsook Chung (Seoul, KR); Sangmo Kim (Hwaseong-si, KR); Hyunjung Kim (Suwon-si, KR); Soonok Jeon (Seoul, KR); Yongsik Jung (Yongin-si, KR); Miyoung Chae (Suwon-si, KR); Dalho Huh (Suwon-si, KR); Hosuk Kang (Suwon-si, KR); Jongsoo Kim (Suwon-si, KR)

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

H01L51/0072 C07D405/10 C07D405/14 C07D409/10 C07D491/048 C07D495/04 C09K11/025 C09K11/06 H01L51/008 H01L51/009 H01L51/0067 H01L51/0071 H01L51/0073 H01L51/0074 H01L51/0085 C09K2211/1007 C09K2211/1022 C09K2211/1044 H01L51/506 H01L51/5016 H01L51/56

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Quick Facts

Patent No.: US 10,593,891
App. No.: 15/234,089
Granted: Mar 17, 2020
Kind: B2

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Abstract

A condensed cyclic compound represented by Formula 1: wherein, in Formula 1, groups and variables are the same as described in the specification.

Claims (175)

1. A condensed cyclic compound represented by Formula 1:

wherein, in Formula 1,

X 1 is selected from a single bond, O, S, N(R 11 ) and C(R 12 )(R 13 ),

X 2 is O or S,

ring A 1 to ring A 4 are each independently a C 5 -C 60 carbocyclic group or a C 2 -C 60 heterocyclic group,

ring A 5 is selected from a benzene, a pyridine, a pyrimidine, a pyrazine, a pyridazine and a triazine,

provided that when n is 0,

1) ring A 1 to ring A 5 are not simultaneously a benzene, or

2) i) one or more of groups R 1 in the number of a1, ii) one or more groups R 2 in the number of a2, iii) one or more of groups R 3 in the number of a3, iv) one or more groups R 4 in the number of a4, v) one or more of groups R 5 in the number of a5, or vi) any combination thereof are each independently a cyano group-substituted C 6 -C 10 aryl group,

R 1 to R 6 and R 11 to R 13 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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted C 2 -C 60 heteroarylalkyl 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 4 )(Q 5 ) and —B(Q 6 )(Q 7 ),

a1 is an integer of 1 to 4,

a2 to a6 are each independently an integer of 0 to 4,

L 1 is selected from

a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group and a triazinylene group; and

a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group and a triazinylene group, each substituted with at least one 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 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group and —Si(Q 8 )(Q 9 )(Q 10 ),

b1 is an integer of 1 to 3,

n is an integer of 0 to 3,

the number of cyano groups in Formula 1 is 1, 2, 3 or 4,

at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted C 1 -C 60 alkoxy group, substituted C 3 -C 10 cycloalkyl group, substituted C 1 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 1 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 7 -C 60 arylalkyl group, substituted C 1 -C 60 heteroaryl group, substituted C 1 -C 60 heteroaryloxy group, substituted C 1 -C 60 heteroarylthio group, substituted C 2 -C 60 heteroarylalkyl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from

a deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 selected from a deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl 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 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl 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 ); and

Q 1 to Q 10 , Q 11 to Q 17 , Q 21 to Q 27 and Q 31 to Q 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 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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted C 2 -C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

2. The condensed cyclic compound of claim 1 , wherein X 1 is a single bond.

3. The condensed cyclic compound of claim 1 , wherein

ring A 1 to ring A 4 are each independently selected from a benzene, a pyridine, a pyrimidine, a pyrazine, a pyridazine, a naphthalene, a quinoline, an isoquinoline, a quinoxaline, a quinazoline, a cinnoline, an indene, an indole, a benzofuran, a benzothiophene, a fluorene, a carbazole, a dibenzofuran and a dibenzothiophene.

4. The condensed cyclic compound of claim 1 , wherein

ring A 1 and ring A 2 are each independently selected from a benzene, a dibenzofuran and a dibenzothiophene, and

ring A 3 and ring A 4 are each independently selected from a benzene, a fluorene, a carbazole, a dibenzofuran and a dibenzothiophene.

5. The condensed cyclic compound of claim 1 , wherein

R 1 to R 6 and R 11 to R 13 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 C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group;

a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group, each substituted with at least one 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 and a phosphoric acid group or a salt thereof;

a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group and a triazinyl group;

a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group and a triazinyl group, each substituted with at least one 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 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group and —Si(Q 31 )(Q 32 )(Q 33 ); and

—Si(Q 1 )(Q 2 )(Q 3 ), and

Q 1 to Q 3 and Q 31 to Q 33 are each independently selected from a hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group and a triazinyl group.

6. The condensed cyclic compound of claim 1 , wherein

R 1 to R 6 and R 11 to R 13 are each independently selected from

a hydrogen, a deuterium, a cyano group, a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group;

a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group, each substituted with at least one selected from a deuterium and a cyano group;

a phenyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group;

a phenyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group, each substituted with at least one selected from a deuterium, a cyano group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and —Si(Q 31 )(Q 32 )(Q 33 ); and

—Si(Q 1 )(Q 2 )(Q 3 ), and

Q 1 to Q 3 and Q 31 to Q 33 are each independently selected from a hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group.

7. The condensed cyclic compound of claim 1 , wherein

L 1 is selected from

a phenylene group, a pyridinylene group, a pyrimidinylene group and a triazinylene group; and

a phenylene group, a pyridinylene group, a pyrimidinylene group and a triazinylene group, each substituted with at least one selected from a deuterium, a cyano group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and —Si(Q 8 )(Q 9 )(Q 10 ), and

Q 8 to Q 10 are each independently selected from a hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group.

8. The condensed cyclic compound of claim 1 , wherein

L 1 is selected from groups represented by Formulae 3-1 to 3-40:

wherein, in Formulae 3-1 to 3-40,

Z 1 is selected from a hydrogen, a deuterium, a cyano group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and —Si(Q 8 )(Q 9 )(Q 10 ),

Q 8 to Q 10 are each independently selected from a hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group,

d4 is an integer of 0 to 4,

d3 is an integer of 0 to 3,

d2 is an integer of 0 to 2, and

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

9. The condensed cyclic compound of claim 1 , wherein n is 0 or 1.

10. The condensed cyclic compound of claim 1 , wherein

the condensed cyclic compound is represented by one of Formulae 1A to 1H:

wherein, in Formulae 1A to 1H, 2A and 2B,

X 1 , X 2 , ring A 1 , ring A 2 , ring A 5 , R 1 to R 6 , a1 to a6, L 1 , b1 and n are the same as in claim 1 ,

ring A 3 is selected from a benzene, a pyridine, a pyrimidine, a pyrazine, a pyridazine, an indene, an indole, a benzofuran, a benzothiophene, a fluorene, a carbazole, a dibenzofuran and a dibenzothiophene,

ring A 6 is represented by Formula 2A,

ring A 7 is represented by Formula 2B,

X 4 is selected from O, S, N(R 4c ) and C(R 4d )(R 4e ),

R 4a to R 4e are the same as R 4 ,

aa4 is an integer of 0 to 3, and

ab4 is an integer of 0 to 2.

11. The condensed cyclic compound of claim 1 , wherein

the condensed cyclic compound is represented by one of Formulae 1-1 to 1-19:

in Formulae 1-1 to 1-19,

X 1 , X 2 , ring A 5 , R 1 to R 6 , a1 to a6, L 1 , b1 and n are the same as in claim 1 ,

X 3 is selected from O, S, N(R 3c ) and C(R 3d )(R 3e ),

X 4 is selected from O, S, N(R 4c ) and C(R 4d )(R 4e ),

X 5 is selected from O, S, N(R 2c ) and C(R 2d )(R 2e ),

R 2a to R 2e are the same as the R 2 ,

R 3a to R 3e are the same as R 3 ,

R 4a to R 4e are the same as R 4 ,

aa2 and aa3 are each independently an integer of 0 to 2,

ab2 and ab3 are each independently an integer of 0 to 4,

aa4 is an integer of 0 to 3, and

ab4 is an integer of 0 to 2.

12. The condensed cyclic compound of claim 1 , wherein

the condensed cyclic compound is represented by one of Formulae 1(1) to 1(12):

wherein, in Formulae 1(1) to 1(12),

X 1 , X 2 , ring A 1 to ring A 5 , R 1 to R 6 , L 1 , b1 and n are the same as in claim 1 , and

a1 to a6 are each independently an integer of 0 to 3.

13. The condensed cyclic compound of claim 12 , wherein

X 1 is a single bond,

ring A 1 and A 2 are each independently selected from a benzene, a dibenzofuran and a dibenzothiophene, and at least one of ring A 1 and A 2 is a benzene,

ring A 3 and A 4 are each independently selected from a benzene, a fluorene, a carbazole, a dibenzofuran and a dibenzothiophene, and at least one of ring A 3 and A 4 is a benzene,

ring A 5 is a benzene,

R 1 to R 6 are each independently selected from

a hydrogen, a deuterium, a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group;

a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group, each substituted with at least one deuterium;

a phenyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group;

a phenyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group, each substituted with at least one selected from a deuterium, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and —Si(Q 31 )(Q 32 )(Q 33 ); and

—Si(Q 1 )(Q 2 )(Q 3 ),

L 1 is selected from

a phenylene group, a pyridinylene group, a pyrimidinylene group and a triazinylene group; and

a phenylene group, a pyridinylene group, a pyrimidinylene group and a triazinylene group, each substituted with at least one selected from a deuterium, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and —Si(Q 8 )(Q 9 )(Q 10 ),

b1 is 1 or 2,

n is 0 or 1, and

Q 1 to Q 3 , Q 31 to Q 33 , and Q 8 to Q 10 are each independently selected from a hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group.

14. The condensed cyclic compound being one of Compounds 10 to 12, 47, 48, 50, 58 to 59, 61 to 64 and 75 to 482:

15. 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 at least one condensed cyclic compound represented by Formula 1 of claim 1 .

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

the first electrode is an anode,

the second electrode is a cathode, and

the organic layer comprises a hole transport region disposed between the first electrode and the emission layer, and an electron transport region disposed between the emission layer and the second electrode,

wherein the hole transport region comprises at least one selected from a hole injection layer, a hole transport layer and an electron blocking layer, and

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

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

the emission layer comprises the at least one condensed cyclic compound represented by Formula 1.

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

the emission layer comprises the at least one condensed cyclic compound represented by Formula 1 and a phosphorescent dopant,

wherein an amount of the at least one condensed cyclic compound is greater than an amount of the phosphorescent dopant.

19. The organic light-emitting device of claim 17 , wherein the emission layer emits blue light.

20. A condensed cyclic compound represented by Formula 1:

wherein, in Formula 1,

X 1 is selected from a single bond, O, S, N(R 11 ) and C(R 12 )(R 13 ),

X 2 is O or S,

ring A 1 to ring A 4 are each independently a C 5 -C 60 carbocyclic group or a C 2 -C 60 heterocyclic group,

ring A 5 is selected from a benzene, a pyridine, a pyrimidine, a pyrazine, a pyridazine and a triazine,

provided that when n is 0,

1) ring A 1 to ring A 5 are not simultaneously a benzene, or

R 1 to R 6 and R 11 to R 13 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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted C 2 -C 60 heteroarylalkyl 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 4 )(Q 5 ) and —B(Q 6 )(Q 7 ),

a1 is an integer of 1 to 4,

a2 to a6 are each independently an integer of 0 to 4,

L 1 is selected from

a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group and a triazinylene group; and

b1 is an integer of 1 to 3,

n is an integer of 0 to 3,

the number of cyano groups in Formula 1 is 2, 3 or 4,

provided that, when one group of R 5 in the number of a5 is a cyano group, one or more of groups R 3 in the number of a3 and one or more of groups R 4 in the number of a4 are not a cyano group,

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

21. A condensed cyclic compound represented by Formula 1:

wherein, in Formula 1,

X 1 is selected from a single bond, O, S, N(R 11 ) and C(R 12 )(R 13 ),

X 2 O or S,

ring A 1 to ring A 4 are each independently a C 5 -C 60 carbocyclic group or a C 2 -C 60 heterocyclic group, and at least one of ring A 1 to ring A 4 is each independently a fluorene, a carbazole, a dibenzofuran or a dibenzothiophene,

ring A 5 is selected from a benzene, a pyridine, a pyrimidine, a pyrazine, a pyridazine and a triazine,

a1 is an integer of 1 to 4,

a2 to a6 are each independently an integer of 0 to 4,

L 1 is selected from

a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group and a triazinylene group; and

b1 is an integer of 1 to 3,

n is an integer of 0 to 3,

the number of cyano groups in Formula 1 is 1, 2, 3 or 4,

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

Assignments (3)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2019

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

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

Reel/Frame 051366/0480 →

CORRECTIVE ASSIGNMENT TO CORRECT THE 8TH INVENTOR NAME PREVIOUSLY RECORDED AT REEL: 039403 FRAME: 0264. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Aug 30, 2016

From: CHUNG, YEONSOOK; KIM, SANGMO; KIM, HYUNJUNG; JEON, SOONOK; JUNG, YONGSIK; CHAE, MIYOUNG; HUH, DALHO; KANG, HOSUK; KIM, JONGSOO

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

Reel/Frame 039872/0266 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 11, 2016

From: CHUNG, YEONSOOK; KIM, SANGMO; KIM, HYUNJUNG; JEON, SOONOK; JUNG, YONGSIK; CHAE, MIYOUNG; HUH, DALHO; HOSUK, HOSUK; KIM, JONGSOO

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

Reel/Frame 039403/0264 →

Priority Claims (1)

KR 10-2015-0114548 · Aug 13, 2015 · national

Continuity (1)

Related Publication 20170047526A1 · Feb 16, 2017